Colored, radiation-curable compositions

ABSTRACT

Radiation-curable compositions, and methods of making the same, for providing a wide variety of substrates with a durable, colored coating or colorant are disclosed. The color is at least in part provided by chromophore molecules that are covalently bonded to other components within the radiation-curable composition. A telecommunication element having a durable color identifying polymeric coating thereon is also disclosed. The telecommunication element comprises an elongated communication transmission medium, such as an optical fiber or an optical fiber ribbon, and a radiation-cured polymeric coating having an identifying color applied on at least a portion of the transmission medium.

CROSS-REFERENCE TO RELATED APPLICATION

This application is a continuation-in-part of co-pending applicationSer. No. 09/870,482, which is a continuation-in-part of co-pendingapplication Ser. No. 09/360,951.

This application discloses and claims subject matter from the followingapplications:

-   -   1) Co-pending application Ser. No. 09/870,482 filed Jun. 1, 2001    -   2) Co-pending application Ser. No. 09/360,951 filed Jul. 27,        1999;    -   3) Co-pending PCT application No. PCT/US 01/05814 filed Mar. 16,        2001; and    -   4) Co-pending provisional application Ser. No. 60/356,160 filed        Feb. 14, 2002. The disclosures of these applications are        incorporated herein by reference.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to colored, radiation-curable compositionsfor use in a wide variety of applications, including colored,radiation-curable coating compositions for telecommunications elements,such as optical fibers and optical fiber ribbons, and colored,radiation-curable ink compositions for other applications, such astextile, electronics, and printing applications. More particularly, thepresent invention relates to colored, radiation-curable compositions forproducing a cured, colored coating on a substrate, such as atelecommunications element, the cured compositions having an identifyingcolor provided by chromophore-containing compounds that are covalentlybonded to other components within the cured composition.

2. Description of Related Art

For many years now, optical fibers have been used as a reliabletransmission medium in telecommunications cables. Typically, an opticalfiber comprises a core, a cladding and one or more coatings applied overthe cladding.

One purpose of the coatings is to protect the surface of the opticalfiber from mechanical scratches and abrasions typically caused bysubsequent handling and use. Another purpose of the coatings is toprotect the glass from exposure to moisture. The coating or coatings mayalso have some influence over the fiber's optical characteristicsbecause the coatings are physically responsive to external mechanicalforces and temperature. The coating compositions applied to the opticalfiber are typically liquid, radiation-curable compositions. Typically,the coating compositions are cured on the optical fiber by exposing thecoating composition to ultraviolet radiation, electron beam radiation orionizing radiation for a predetermined period of time deemed suitablefor effective curing.

Telecommunications cables containing optical fibers come in a variety ofconfigurations. In some cables, the optical fibers are held looselyinside a buffer tube. In other cables, the optical fibers are arrangedin a planar array to form an optical fiber ribbon. The planar array istypically encapsulated by one or more radiation-curable matrix materiallayers. The radiation-curable matrix layers are cured by exposing thematrix material to ultraviolet radiation, electron beam radiation,ionizing radiation or infrared radiation for a predetermined period oftime deemed suitable for effective curing.

In a telecommunications cable containing multiple optical fibers, theoptical fibers may be distinguished from each other by the use of acolor coating layer which has been applied over a coated optical fiber.Colors in the color coating layer are usually obtained by dispersingcolored pigment particles in a suitable liquid carrier and applying theliquid carrier over the coating. Alternatively, the optical fibers maybe distinguished from each other by the use of a so-called coloredprimary coating, which is a colored coating applied directly onto anoptical fiber.

Unfortunately, the use of pigment particles to provide color in colorcoatings for optical fibers has presented manufacturing and performanceproblems. For example, the pigment particles and the liquid carrier tendto gradually separate into two distinct phases. As a result, pigmentedcolor coatings have a relatively short shelf life.

In addition, the phase separation in a pigmented coloring system isfurther complicated by the concurrent agglomeration of pigmentparticles. Undesirably, the presence of pigment particle agglomerates ina color coating on a coated optical fiber can induce micro-bending whichresults in transmission losses.

Typically, a relatively high concentration of pigment material isrequired to achieve an opaque or translucent ultravioletradiation-curable color coating. Unfortunately, the required highconcentration inhibits the transmission of incident ultravioletradiation which is necessary to cure the color coating material becausethe pigments refract, reflect and scatter the incident radiation. Theinhibition of the ultraviolet radiation results in a reduction inprocessing speed of the optical fiber along a manufacturing line andthereby increases production costs. Also, the slow cure speed ofpigmented color coatings causes the processing and the cure of thesematerials to be sensitive to minor changes in the thickness of the colorcoatings.

The use of dyes to provide color in color coatings has been consideredas an alternative to pigment-based color coatings. Dyes have theadvantage over pigments of faster curing because the dyes do not scatterthe curing radiation, although some dyes may absorb light which couldslow curing. Dyes, however, are generally not preferred because theydiffuse (bleed) out into common cable filling compounds resulting in acolor loss. In an effort to reduce the bleeding, U.S. Pat. No. 5,074,643teaches the use of a polymeric dye in a color coating. The polymericdyes are macromolecular chromophore-containing molecules that becomeentrapped in the cross-linked coating network. While the entrapmentresults in a slowing of the bleeding process, the dyes neverthelessstill bleed. Over time, even with the entrapped polymeric dyes, thecolor imparted to the fibers is likely to be lost and if the color islost from the fibers, then identification of each of the fibers becomesextremely difficult and time-consuming in the field duringfiber-splicing.

The color imparted to the fibers will be lost over time if the dyesthemselves lack stability. In particular, the dyes should havesufficient thermal stability and light fastness to impart the desiredcolor for an extended period of time.

If a telecommunications cable has many optical fiber ribbons, it isgenerally desirable to distinguish one optical fiber ribbon from anotherby coloring each of the optical fiber ribbons. Typically, color in acolored optical fiber ribbon is obtained in the same way as color isobtained in a color-coated optical fiber. The optical fiber ribbonmatrix composition is either provided with pigments or a polymer dye isused. The same problems mentioned above with respect to colored opticalfibers apply to colored optical fiber ribbons.

It is desirable to provide a composition that can provide a durablecured color coating that can be used for color coding atelecommunications element, such as an optical fiber, where the coatinghas the ability to withstand the conditions in a typical operationalenvironment that such elements are typically found. It would also bedesirable to provide a composition that can provide a durable cured ink,dye, coating, colorant, etc. that can be used for substrates in otherfields, such as textiles, electronics, or printing, where the ink, dye,coating, colorant, etc. has the ability to withstand the conditions in atypical operational environment that such substrates are typicallyfound. The present invention provides such a composition.

SUMMARY OF THE INVENTION

In one aspect of the present invention, there is provided achromophore-containing compound, wherein the chromophore-containingcompound comprises one or more functional groups that are capable ofbeing reacted to covalently bond the chromophore-containing compoundwith any another molecule or series of molecules in a radiation-curablecomposition, such that the chromophore-containing compound isincorporated via covalent bonding into the radiation-cured composition.

In one embodiment of the first aspect of the invention, thechromophore-containing compound includes, as one or more functionalgroups, one or more radiation-curable groups. The chromophore-containingcompound comprising one or more radiation-curable groups becomescovalently bonded by one or more covalent bonds to other constituents ofa radiation-curable composition during the curing step.

In a second embodiment of the first aspect of the invention, thechromophore-containing compound is a colored oligomer. For example,there may be provided a chromophore-containing compound comprising achromophore covalently bonded to or within an oligomeric backbone, suchthat the chromophore of the chromophore-containing compound is attachedto the remainder of the oligomer by one or more covalent bonds. Thecolored oligomer may include radiation-curable groups that becomecovalently bonded to other constituents of a radiation-curablecomposition during the curing step.

In another aspect of the present invention, there is provided aradiation-curable composition comprising a chromophore-containingcompound, wherein the chromophore-containing compound comprises one ormore functional groups that are capable of reacting to covalently bondthe chromophore-containing compound with any another molecule or seriesof molecules in the radiation-curable composition. Upon being subjectedto the appropriate level of radiation, the radiation-curable compositionprovides a radiation-cured composition having a chromophore-containingcompound covalently bonded to other molecules or series of moleculeswithin the radiation-cured composition.

In yet another aspect of the invention, there is provided a colorconcentrate, or masterbatch, comprising the chromophore-containingcompound, wherein the color concentrate or masterbatch is a vehicle forthe delivery of the chromophore-containing compound to the particularlydesired application or embodiment. There is also provided a method formanufacturing such a color concentrate or masterbatch.

In a further aspect of the present invention, there is provided atelecommunication element having a color-identifying coating thereon,the telecommunication element comprising an elongated communicationtransmission medium and a coating having an identifying color applied onat least a portion of the transmission medium, wherein the coatingcomprises a radiation-cured, crosslinked polymeric network, and whereinthe identifying color in the coating is provided by at least onechromophore molecule covalently bonded by at least one covalent bond tothe polymeric network. The color of a telecommunication element preparedin this manner according to the invention does not bleed in the presenceof cable-filling compounds. For example, the telecommunication elementmay be an optical fiber ribbon, and the ribbon has a colored matrix or acolored coating applied over an uncolored matrix, wherein the color ofthe colored matrix or colored coating does not bleed in the presence ofcable-filling compounds.

It is a still further aspect of the present invention to provide: amethod for producing a colored, radiation-curable composition having atleast one chromophore-containing compound, wherein thechromophore-containing compound comprises one or more functional groupsthat are capable of being reacted to covalently bond thechromophore-containing compound with any another molecule or series ofmolecules in the radiation-curable composition; and a method ofproviding at least a portion of a substrate with a radiation-curedcomposition having at least one chromophore-containing compound, whereinthe chromophore-containing compound is covalently bonded to othermolecules or series of molecules within the radiation-cured composition.

The method may comprise the steps of: providing a substrate, such as,for example, a transmission medium; providing a colored,radiation-curable composition comprising a chromophore-containingcompound; applying the radiation-curable composition to at least aportion of the substrate; and exposing the radiation-curable compositionfor a suitable period of time to radiation of a suitable wavelength andintensity to cause curing of the composition into a radiation-cured,crosslinked polymeric network, wherein the identifying color in thecoating is provided by at least one chromophore molecule covalentlybonded by at least one covalent bond to the polymeric network.

The invention will be more fully understood when reference is made tothe following detailed description taken in conjunction with theaccompanying drawings.

BRIEF DESCRIPTION OF THE DRAWINGS

The drawings, not drawn to scale, include:

FIG. 1A, which is a cross-sectional view of an optical fiber coated withprimary and secondary coatings;

FIG. 1B, which is a cross-sectional view of an optical fiber coated withprimary, secondary and tertiary coatings; and

FIG. 2, which is a cross-sectional view of a splittable optical fiberribbon containing at least one colored matrix.

DETAILED DESCRIPTION OF THE PRESENT INVENTION

Typical telecommunications elements include an elongated transmissionmedium such as a metallic wire or an optical fiber. Referring to FIG.1A, a typical optical fiber 10 transmission medium is shown. The typicaloptical fiber 10 is formed by a glass core 12 which is surrounded by aglass cladding 14. The glass cladding 14 of the optical fiber 10 isusually surrounded by one or more protective polymeric coatings, e.g.,primary and secondary polymeric coatings, or primary, secondary, andtertiary polymeric coatings.

For example, as shown in FIG. 1A, an inner protective polymeric coating16 covers at least a portion of the cladding 14 and an outer protectivepolymeric coating 18 typically covers at least a portion of the innercoating 16. The inner 16 and outer 18 protective coatings may bereferred to as inner primary and outer primary coatings, or primary andsecondary coatings. The inner coating 16 is usually obtained by applyinga radiation-curable (polymerizable) composition capable of forming apolymeric coating upon curing over the cladding 14.

The radiation-curable composition is normally applied by passing theoptical fiber through a first die or a coating applicator usingtechniques well known in the art, and therefore, not described herein.Once the radiation-curable composition is applied over the cladding 14,the composition may be cured by exposing it to radiation, such asultraviolet radiation, electron beam radiation or ionizing radiation, toinitiate curing (polymerization) thereof. Ultraviolet radiation is mostcommonly used.

The application and curing of the radiation-curable composition to formthe inner coating 16 may be followed by the application and curing ofanother radiation-curable composition capable of forming a polymericcoating which forms the outer coating 18. This sequence is known as awet-on-dry application of the outer coating 18. Alternatively, theapplication of the radiation-curable composition which forms the innercoating 16 may be directly followed by the application of aradiation-curable composition forming the outer coating 18 prior toexposure to the curing radiation. This is known in the art as awet-on-wet application. Each application technique is well known in theart.

As used herein, the term “primary coating” is defined as that coatingwhich directly contacts the glass portion of the optical fiber. Theuncured primary coating should be liquid at room temperature. Theuncured primary coating should have a viscosity suitable for high speedprocessing, and the uncured primary coating should have a high curespeed. The cured primary coating should exhibit good adhesion to glassto prevent premature delamination of the coating from the glass portionof the optical fiber. The cured primary coating should have a lowmodulus at lower temperatures to minimize the effects of microbendattenuation due to small stresses on the optical fiber itself.

As used herein, the term “secondary coating” is defined as the coatingwhich covers the primary coating on the optical fiber. The curedsecondary coating should have sufficient modulus to give impactresistance and to provide a protective barrier, and give tensilestrength to the optical fiber. The cured secondary coating shouldexhibit little physical change over a wide temperature range and goodresistance to water and solvent absorption. For cases where thesecondary coating is a colored secondary coating, it should exhibit goodcolor stability.

The uncured liquid primary or secondary coating composition should havea sufficiently low viscosity that the composition will be easily appliedto form a continuous protective coating on the glass fibers. Examples ofsuch viscosity of an order of magnitude from about 10³ cP at 45-50° C.,e.g., from about 2×10³ to about 8×10³ cP at room temperature. There isno particular limitation on viscosity, however, and it can be adjustedto a given application by known methods. For example, viscosity can beadjusted depending on the type of optical fiber material beingformulated and the method of application, including the processingtemperature employed.

Generally, the thickness of the cured primary or secondary coating willbe dependent on the intended use of the optical fiber, althoughthicknesses of about 20 to 35 microns and, in particular, thicknesses ofabout 25 to 30 microns are suitable.

When used as primary coatings, cured coatings in accordance with thepresent invention may have a glass transition temperature (T_(g)) offrom about −60° C. to about 0° C., for example, from about −50° C. toabout −30° C., and, e.g. about 40° C., and a low modulus of elasticityof from about 0.5 to about 3.0 MPa at room temperature (20° C.) and 50%relative humidity, for example, from about 1.0 to about 2.5 MPa.

When utilized as a secondary coating, cured coatings in accordance withthe present invention may have a glass transition temperature (T) offrom about 25 C. to about 100° C. The cured secondary coatings may havea T_(g) of from about 50° C. to about 80° C., for example, about 75° C.The cured secondary coatings may have a low modulus of elasticity offrom about 5.0 to about 60 MPa at around 80° C. and 50% relativehumidity, for example, from about 20 to about 40 MPa, and, e.g. about 30MPa.

A typical radiation-curable composition capable of forming a polymericcoating for the inner 16 and outer 18 coatings usually includes anacrylated oligomer, e.g. a urethane acrylate oligomer, which is areaction product of (1) a polyol, such as a polyether diol, polyesterdiol or hydrocarbon diol; (2) a polyisocyanate, such as an aliphaticdiisocyanate; and (3) an endcapping monomer, such as ahydroxyalkylacrylate or a hydroxyalkylmethacrylate. These oligomerstypically have monofunctionality, difunctionality or trifunctionality.Other materials, such as photoinitiators, reactive diluents and adhesionpromotors, such as organofunctional silane adhesion promoters, may beincluded in the radiation-curable composition to tailor the physicalproperties of the composition to meet specific end-use applicationrequirements, such as to provide good thermal, oxidative and hydrolyticstability as well as a soft, compliant, low glass transitiontemperature-type coating. A discussion of radiation-curable primary andsecondary coating compositions may be found in U.S. Pat. No. 5,146,531,which is incorporated in its entirety herein by reference.

While particular reference has been made to the case of atelecommunication element coated with primary and secondary coatings, itis readily understood by one skilled in the art that such elements maybe coated with additional coatings, such as a tertiary coating, or withonly one coating. A tertiary coating is generally thinner than asecondary coating, e.g. 10% as thick as a secondary coating. Thus, atertiary coating may be applied to a thickness of from 2 to 5 microns.

According to the present invention, an uncolored, radiation-curablecomposition that is, for example, applied over the cladding and cured toform an inner coating 16 may be colored by adding to the composition achromophore-containing compound comprising one or more functional groupsthat are capable of reacting to covalently bond the chromophore of thechromophore-containing compound to any another molecule or series ofmolecules in the radiation-curable composition.

The chromophore moiety of the chromophore-containing compound may beselected from, e.g., dye chemical families including the following,non-exhaustive chemistries: anthraquinone, methine, and azo. Whether thechromophore moiety of the chromophore-containing compound isanthraquinone-type, methine-type, azo-type, mixtures thereof, or someother type, the selected chromophore moiety of thechromophore-containing compound preferably exhibits good thermalstability and light fastness. Furthermore, the chromophore moiety of thechromophore-containing compound is not limited by molecular weight. Itmay be a monomeric moiety comprising a chromophore, or it may be anoligomeric moiety comprising a chromophore within the backbone of anoligomeric chain or comprising a chromophore as an end or side group ofan oligomeric chain.

In general, the functional group(s) of a chromophore-containing compoundaccording to the invention is any group capable of reacting tocovalently bond the chromophore of the chromophore-containing compoundto any another compound or series of compounds within aradiation-curable composition, such that the chromophore molecule itselfis incorporated into the radiation-curable composition. For example, thechromophore-containing compound may comprise a radiation-curablefunctional group, e.g., ethylenic unsaturation such as an acrylategroup, which, when exposed to radiation, covalently bonds with othersimilar groups in a radiation-curable composition.

In a particular embodiment, the functional group(s) of achromophore-containing compound according to the invention is capable ofreacting with a radiation-curable-group-containing monomer or oligomerto form a radiation-curable monomer or oligomer comprising a chromophorecovalently bonded by at least one covalent bond to the monomer oroligomer. The radiation-curable monomer or oligomer comprising thecovalently bonded chromophore may itself become covalently bonded to anyother compound or series of compounds, such as, for example, anon-chromophore-containing, radiation-curable monomer or oligomer,within a radiation-curable composition.

For example, a radiation-curable monomer or oligomer comprising achromophore covalently bonded thereto may also have a radiation-curableend group(s) or side group(s). When exposed to radiation, this endgroup(s) or side group(s) covalently bonds with compounds containingsimilar groups in the radiation-curable composition. As a particularexample, a radiation-curable composition may have compounds containingacrylate groups, vinyl groups or epoxy groups to which aradiation-curable monomer or oligomer comprising a chromophore moleculecovalently bonded thereto can covalently bond.

As a more particular example of the embodiment wherein a functionalgroup(s) of a chromophore-containing compound reacts with aradiation-curable-group-containing monomer or oligomer, there isprovided a chromophore-containing polyol comprising both hydroxyfunctionality and a chromophore molecule covalently bonded thereto. Thechromophore-containing polyol may have ester or carboxy functionality inaddition to the hydroxy functionality. By reacting the polyol comprisinga chromophore moiety covalently bonded thereto with, e.g., an oligomerof a radiation-curable composition, the chromophore becomes incorporatednot only into the radiation-curable oligomer by way of at least onecovalent bond, but ultimately into the cured composition as well.

As a general example of forming a colored monomer or oligomer componentof a colored, radiation-curable composition, a polyol comprising achromophore molecule covalently bonded thereto and hydroxy end groups orside groups is provided, in addition to, or in place of, some or all ofthe typical polyol, e.g. hydrocarbon diol, that is reacted with anisocyanate, e.g., an aliphatic diisocyanate, and a radiation-curablemonomer(s) to form a typical acrylated oligomer reaction product used ina radiation-curable composition for, e.g., optical fiber coatings.Examples of suitable polyols comprising a chromophore moleculecovalently bonded thereto are dyes marketed under the trademarkREACTINT™ by the Milliken Chemical Company. Those skilled in the artwill now recognize that if a sufficient amount of a polyol comprising achromophore molecule covalently bonded thereto is reacted with anisocyanate and radiation-curable monomer, then the resulting acrylatedmonomer or oligomer will be colored in accordance with the color of thechromophore molecule(s) (or blend of chromophore molecules for certaincolors within the spectrum of colors) that has been covalently bonded tothe monomer or oligomer.

A radiation-curable composition comprising a chromophore-containingcompound according to the invention, e.g., a colored, acrylated monomeror oligomer, may be applied, e.g., directly to the cladding of theoptical fiber as a colored, radiation-curable composition to form theinner coating 16 or it may be applied directly over a previously appliedinner coating as the outer coating 18. Those skilled in the art willrecognize that the radiation-curable composition comprising achromophore-containing compound according to the invention, e.g., acolored monomer or oligomer, may also be applied over a previouslyapplied outer coating as a tertiary coating 20, which is illustrated inFIG. 1B. Alternatively, the radiation-curable composition comprising achromophore-containing compound according to the invention, e.g., acolored, acrylated monomer or oligomer, may be applied onto or into aribbon matrix, producing a colored optical fiber ribbon.

In a commercially advantageous alternative, chromophore-containingcompounds according to the invention, e.g., colored, acrylated monomersor oligomers, are blended or diluted with non-chromophore-containinganalogs that are present in a commercially available, uncolored,radiation-curable composition, such as those compositions typicallyformulated to provide a protective coating on an optical fiber, so thatthe combination of the chromophore-containing compounds according to theinvention and the non-chromophore-containing analogs forms a colored,radiation-curable composition which can be applied, e.g., over thecladding 14, the inner coating 16 or the outer coating 18 of the opticalfiber (or onto or into a ribbon matrix). Such radiation-curablecompositions may additionally include one or more uncolored acrylateoligomers, a reactive diluent, one or more photoinitiators,organofunctional silane adhesion promoters, pigments, e.g., TiO₂,stabilizers, etc. In other words, the chromophore-containing compoundsdescribed herein may be added, in a quantity sufficient to impart color,to a commercially known, uncolored, radiation-curable composition, suchas those used to provide a protective coating over an optical fiber.

After the radiation-curable composition containing thechromophore-containing compounds, e.g., the colored monomers and/oroligomers, is cured, i.e., polymerized, by exposure to radiation of asuitable wavelength and intensity for a suitable period of time, theresulting cured composition contains chromophore molecules which arecovalently bonded thereto. Because the chromophore molecules arecovalently bonded to other components within the cured composition, therisk of color loss due to bleeding is negligible. Thus, themanufacturing advantages that a dye provides over pigments, e.g.application and cure speed, can be obtained while avoiding the bleedingdisadvantages that a dye which is not covalently bonded may have whenused in an optical fiber environment, or in any other workingenvironment.

According to one embodiment, a chromophore-containing compound isprovided which may be suited, amongst other applications, for impartingcolor to a telecommunication element, such as a coated optical fiber orcoated optical fiber ribbon. The chromophore-containing compound may beformed via, e.g., isocyanate chemistry. For example, achromophore-containing compound comprising an isocyanate-reactivefunctional group(s), e.g., —OH, —NH₂ and —SH, may be reacted with anisocyanate comprising a radiation-curable group, e.g., comprisingethylenic unsaturation. An example of an isocyanate comprising aradiation-curable group is meta-isopropenyl-α,α-ethyl isocyanate, butany monoisocyanate or polyisocyanate, including a diisocyanate, may beemployed, provided that it comprises a radiation-curable group.

According to another embodiment, a particular type ofchromophore-containing compound, i.e., a chromophore-containingoligomer, is provided which may be suited, amongst other applications,for imparting color to a communications element, such as a coatedoptical fiber. This chromophore-containing oligomer may be formed inseveral manners. For example, the chromophore moiety of thechromophore-containing oligomer may be bonded by one covalent bond tothe remainder of the oligomer, such that the chromophore moiety isprovided as an end group or side group of the oligomer. Alternatively,the chromophore moiety of the chromophore-containing oligomer may bebonded by a pair of covalent bonds to the remainder of the oligomer,such that the chromophore moiety is provided as part of the backbone ofthe oligomer.

An example for providing a chromophore-containing oligomer having thechromophore moiety as part of the backbone of the oligomer includes astep of forming an oligomer precursor having at least two terminalisocyanate groups. This oligomer precursor may be said to be end-cappedwith isocyanate groups.

The isocyanate-end-capped oligomer may be converted into an oligomerend-capped with radiation-curable groups. For example, theisocyanate-end-capped oligomer precursor may be reacted with aradiation-curable monomer including both (i) a reactive functionalitywhich is reactive with the isocyanate groups of theisocyanate-end-capped oligomer precursor and (ii) a radiation-curablefunctionality, including ethylenic unsaturation. Groups which arereactive with isocyanate groups include —OH, —NH₂ and —SH. The reactionwith the isocyanate groups generates covalent linkages. For example, thereaction of an —OH group with an isocyanate group creates a urethanelinkage, and the reaction of an —NH₂ group with an isocyanate groupcreates a urea linkage.

The isocyanate-end-capped oligomer precursor is prepared by reacting atleast one isocyanate, such as a polyisocyanate, e.g., diisocyanate, withat least one polyfunctional compound having at least twoisocyanate-reactive groups, such as —OH, —NH₂ and —SH. A particularpolyfunctional compound of this type is a diol.

At least a portion of the polyfunctional compound, e.g., diol, includesa chromophore, such as an anthraquinone, methine or azo chromophore. Forexample, suitable examples of anthraquinone chromophores are given in anarticle entitled “Dyes, Anthraquinone” at pages 212-279 of theKirk-Othmer Encyclopedia of Chemical Technology, Third Edition, Volume8, 1979.

A particular example of a polyfunctional compound including achromophore is an anthraquinone dye having the following formula:

-   -   wherein the R groups R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸, are each        independently selected from the group consisting of hydrogen,        amino, hydroxy, halogen, nitro, carboxylated alkali metal,        sulfated alkali metal and a hydrocarbyl group optionally        containing one or more heteroatoms, provided that at least two        of groups R¹ through R⁸ have at least one isocyanate-reactive        functionality selected from the group consisting of —OH, —NH₂        and —SH, and further wherein adjacent R groups from amongst R        groups R¹ through R⁸ may form a ring.

An example of a compound wherein adjacent R groups from amongst R groupsR¹ through R⁸ form a ring is a compound wherein R¹ and R² combine toform a benzene ring.

When an R group from amongst R groups R¹ through R⁸ is a hydrocarbylgroup including a heteroatom, the heteroatom may appear anywhere in thegroup, for example, the heteroatom may appear (1) as a linking groupattached directly to the anthraquinone core, (2) as a side group, or (3)as a linking group linking two or more hydrocarbyl groups together.

For example, from 1 to 3 of R groups R¹ through R⁸ may have thefollowing formula:

-   -   wherein R⁹ is hydrogen or an alkyl group having from 1 to about        12 carbon atoms, X is —CH₂—, a is an integer of from 1 to about        6, Y represents polymeric units of hydroxy alkylenes or alkylene        oxide monomers selected from the group consisting of ethylene        oxide, propylene oxide, butylene oxide, cyclohexane oxide, and        glycidol, b is either 0 or 1, and Z is a reactive —OH, —NH₂, or        —SH group.

Specific examples of such anthraquinone dyes are described in U.S. Pat.No. 4,846,846 and may have the following formula:

wherein R⁹ and R¹⁰ are independently selected from hydrogen or an alkylgroup having from 1 to about 12 carbon atoms, X is —CH₂—, a and a′ areindependently selected from integers of from 1 to about 6, Y and Y′ areindependently selected from polymeric units of hydroxy alkylenes oralkylene oxide monomers selected from the group consisting of ethyleneoxide, propylene oxide, butylene oxide, cyclohexane oxide, and glycidol,b and b′ are independently either 0 or 1, and Z and Z′ are independentlyselected from reactive —OH, —NH₂, or —SH groups.

As described in U.S. Pat. No. 4,846,846, a particular subclass of suchanthraquinone dyes may have the following formula:

wherein n, n′, m, m′, p, and p′ may independently have a value of from 0to about 40.

A particular example of an anthraquinone dye described in U.S. Pat. No.4,846,846 has the following formula:

Other examples of anthraquinone dyes include1,5-bis((3-hydroxy-2,2-dimethylpropyl)amino)-9,10-anthracenedione, whichis a red dye;2,2′-((9,10-dihydro-9,10-dioxo-1,5-anthracenediyl)bis(thio))bis-benzoicacid, 2-hydroxyethyl ester, which is a yellow dye; and1,5-bis((2,2-dimethyl-3-hydroxypropyl)amino)-4,8-bis((4-methylphenyl)thio)anthraquinone, which is a blue dye. Other colors, such as pink, green,black, brown and violet, may be formed by blending these dyes or byblending oligomers containing the same.

There are still further types of chromophore-containing compoundscomprising functional groups that may be used to covalently linkchromophores to the polymeric matrix of coating compositions, inks,colorants, etc. For example, there may be provided a radiation-curableanthraquinone dye comprising an anthraquinone core group with at leastone substituent comprising a radiation-curable group. Theradiation-curable group may be an ethylenically-unsaturated group, suchas a (meth)acrylic group, or an epoxy group.

A radiation-curable anthraquinone dye comprising an anthraquinone coregroup with at least one substituent comprising a radiation-curable groupmay have the following formula:

-   -   wherein the R groups R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶, R¹⁷ and R¹⁸        are each independently selected from the group consisting of        hydrogen, amino, hydroxy, halogen, nitro, carboxylated alkali        metal, sulfated alkali metal and a hydrocarbyl group optionally        containing one or more heteroatoms, provided that at least one        of groups R¹¹ through R¹⁸ have at least one        ethylenically-unsaturated radiation-curable functionality.

For example, one or two of R groups R¹¹ through R¹⁸ may have a(meth)acrylic functionality and at least four of R groups R¹¹ throughR¹⁸ may be hydrogen.

Radiation-curable anthraquinone dyes comprising an anthraquinone coregroup with at least one substituent comprising a radiation-curable groupmay be formed by esterification reactions of hydroxy-functionalanthraquinone dyes with acrylic acid-type monomers. For example, theabove-mentioned dihydroxy functional anthraquinone dyes, i.e.1,5-bis((3-hydroxy-2,2-dimethylpropyl)amino)-9, 10-anthracenedione,2,2′-((9,10-dihydro-9, 10-dioxo-1,5-anthracenediyl)bis(thio))bis-benzoicacid, 2-hydroxyethyl ester, and1,5-bis((2,2-dimethyl-3-hydroxypropyl)amino)-4,8-bis((4-methylphenyl)thio)anthraquinone, could undergo such esterification reactions to form thefollowing compounds, respectively:

-   -   wherein R²⁹, R³⁰, R³¹, R³², R³³, and R³⁴ are the same or        different and are independently hydrogen or a C₁ to C₆ alkyl        optionally substituted with one or more substituents selected        from the group consisting of —OH, —NH₂, —SH, —NO₂, —CN and        halogen.

A radiation-curable, chromophore-containing compound according to theinvention, may be mixed with standard components of a radiation-curablecomposition, such as standard components of radiation-curablecompositions for coating a communications element, e.g., an opticalfiber, an optical fiber ribbon, or a plurality of optical fibersarranged in an array, or standard components of radiation-curablecompositions for forming inks or colorant packages. Such components mayinclude one or more of (1) at least one non-chromophore-containing,radiation-curable compound, (2) at least one photoinitiator, and (3) atleast one reactive diluent.

A specific example of a non-chromophore-containing, radiation-curablecompound is a non-chromophore-containing, radiation-curable oligomer,such as a (meth)acrylate end-capped urethane oligomer, which may be anyone of the polyether-based, aliphatic urethane acrylate compoundscommercially available from UCB Chemical Corp. They are sold under thename EBECRYL, and include EBECRYL 230. EBECRYL 230 is a difunctionalaliphatic urethane acrylate oligomer with a polyether backbone.

Another example of a (meth)acrylate end-capped urethane oligomer is anyone of the polyester-based, aliphatic urethane acrylate oligomers thatare available from Sartomer. They are sold under the name CN966xxx, andinclude CN966J75, a difunctional aliphatic urethane acrylate oligomerwith a polyester backbone. These oligomers are also available fromHenkel Corp., which manufactures PHOTOMER products, including PHOTOMER6010. A polyester polyol, which can be used to make a polyester-basedurethane acrylate oligomer, is DESMOPHEN 2001KS, available from BayerCorp. This product is an ethylene butylene adipate diol.

Alternatively, conventional urethane acrylate oligomers may be formed byreacting a polyol, for example a diol, with a multifunctionalisocyanate, for example a diisocyanate, and then end-capping with ahydroxy-functional (meth)acrylate.

The polyol may be a polyol with a number average molecular weight ofabout 200-10,000, such as polyether polyol, polyester polyol,polycarbonate polyol, and hydrocarbon polyol.

Polyether polyols may be homopolymers or copolymers of alkylene oxidesincluding C₂ to C₅ alkylene oxides such as, for example, ethylene oxide,propylene oxide, butylene oxide, tetrahydrofuran, and3-methyltetrahydrofuran; homopolymers or copolymers of the abovealkylene oxides obtained by using, as an initiator, C₁₄ to C₄₀ polyols,such as 12-hydroxystearyl alcohol and hydrogenated dimerdiol; andadducts of the above alkylene oxides with bisphenol-A or hydrogenatedbisphenol-A. These polyether polyols may be used alone or in combinationof two or more.

Polyester polyols may be, for example, addition reaction products of adiol component and a lactone, reaction products of the diol componentand a polyvalent carboxylic acid, and addition reaction products ofthree components, including the diol component, a dibasic acid, and thelactone. The diol component may be C₂ to C₄₀ aliphatic diols with a lowmolecular weight such as ethylene glycol, propylene glycol, diethyleneglycol, dipropylene glycol, 1,4-butanediol, 1,5-pentanediol,3-methyl-1,5-pentanediol, 2,4-diethyl-1,5-pentanediol, 1,6-hexaneglycol, neopentyl glycol, 1,9-nonanediol, 1,10-decanediol,12-hydroxystearyl alcohol, and hydrogenated dimerdiol; and an alkyleneoxide adduct of bisphenol-A. The lactone may be, for example,epsilon-caprolactone, delta-valerolactone, andbeta-methyl-delta-valerolactone. The polyvalent carboxylic acid may be,for example, aliphatic dicarboxylic acids such as succinic acid, adipicacid, azelaic acid, sebacic acid, and dodecanedioic acid; and aromaticdicarboxylic acids such as hexahydrophthalic acid, tetrahydrophthalicacid, phthalic acid, isophthalic acid, and terephthalic acid.

Polycarbonate polyols may be, for example, polycarbonate diols which areobtainable by a reaction of a short chain dialkylcarbonate and acomponent selected from aforementioned polyether polyols, polyesterpolyols and diol components such as 2-methylpropanediol, dipropyleneglycol, 1,4-butanediol, 1,6-hexanediol, 3-methyl-1,5-pentanediol,neopentyl glycol, 1,5-octanediol, and1,4-bis-(hydroxymethyl)cyclohexane. The short chain dialkylcarbonate maybe C₁-C₄ alkylcarbonates such as, for example, dimethylcarbonate anddiethylcarbonate.

Polyols with a low molecular weight may be used. Examples of polyolswith a low molecular weight include ethylene glycol, propylene glycol,tripropylene glycol, 1,3- or 1,4-butanediol, neopentyl glycol,1,6-hexanediol, 1,9-nonanediol, 1,10-decanediol, higher fatty acidpolyols and higher hydrocarbon polyols such as castor oil, coconut oil,monomyristins (1-monomyristin and 2-monomyristin), monopalmitins(1-monopalmitin and 2-monopalmitin), monostearins (1-monostearin and2-monostearin), monooleins (1-monoolein and 2-monoolein),9,10-dioxystearic acid, 12-hydroxyricinoleyl alcohol, 12-hydroxystearylalcohol, 1,16-hexadecanediol (juniperic acid or a reduction product ofthapcic acid), 1,21-henicosanediol, chimyl alcohol, batyl alcohol,selachyl alcohol and dimeric acid diol.

As previously explained, any of the above-mentioned polyols, which maybe used to prepare conventional (meth)acrylate end-capped oligomers, maybe blended with polyols including chromophoric groups and reacted withisocyanates to form colored oligomers.

An isocyanate used to form a colored or uncolored monomer or oligomer,may be, for example, an aromatic polyisocyanate, an aromatic aliphaticpolyisocyanate, an alicyclic polyisocyanate, or an aliphaticpolyisocyanate. The particular isocyanate selected is not limited bymolecular weight. It may be a so-called monomeric isocyanate, or it maybe an oligomeric isocyanate.

Examples of the aromatic polyisocyanates include diisocyanates such asm-phenylene diisocyanate, p-phenylene diisocyanate, 4,4′-diphenyldiisocyanate, 1,5-naphthalene diisocyanate, 4,4′-diphenylmethanediisocyanate, 2,4- or 2,6-tolylene diisocyanate, 4,4′-toluidinediisocyanate, and 4,4′-diphenyl ether diisocyanate; and polyisocyanatessuch as triphenylmethane-4,4′,4″-triisocyanate,1,3,5-triisocyanatebenzene, 2,4,6-triisocyanatetoluene, and4,4′-diphenylmethane-2,2′,5,5′-tetraisocyanate.

Examples of the aromatic aliphatic polyisocyanates include diisocyanatessuch as 1,3- or 1,4-xylene diisocyanate or mixtures thereof and 1,3- or1,4-bis(1-isocyanate-1-methylethyl)benzene or mixtures thereof; andpolyisocyanates such as 1,3,5-triisocyanatemethylbenzene.

Examples of the alicyclic polyisocyanates include diisocyanates such as1,3-cyclopentene diisocyanate, 1,4-cyclohexane diisocyanate,1,3-cyclohexane diisocyanate,3-isocyanatemethyl-3,5,5-trimethylcyclohexyl isocyanate (isophoronediisocyanate or IPDI), 4,4′-methylenebis(cyclohexyl isocyanate) (H₁₂MDIor DESMODUR W, available from Bayer), methyl-2,4-cyclohexanediisocyanate, methyl-2,6-cyclohexane diisocyanate, and 1,3- or 1,4-bis(isocyanatemethyl)cyclohexane; and polyisocyanates such as1,3,5-triisocyanatecyclohexane, 1,3,5-trimethylisocyanatecyclohexane,2-(3-isocyanatepropyl)-2,5-di(isocyanatemethyl)-bicyclo(2.2.1)heptane,2-3-isocyanatepropyl)-2,6 -di(isocyanatemethyl)-bicyclo(2.2.1)heptane,3-(3-isocyanatepropyl)-2,5-di(isocyanatemethyl)-bicyclo(2.2.1)heptane,5-(2-isocyanateethyl)-2-isocyanatemethyl-3-(3-isocyanatepropyl)-bicyclo(2.2.1)heptane,6-(2-isocyanateethyl)-2-isocyanatemethyl-3-(3-isocyanatepropyl)-bicyclo(2.2.1)heptane,5-(2-isocyanateethyl)-2-isocyanatemethyl-2-(3-isocyanatepropyl)-bicyclo(2.2.1)heptane,and6-2-isocyanateethyl)-2-isocyanatemethyl)-2-(3-isocyanatepropyl)-bicyclo(2.2.1)heptane.

Examples of the aliphatic polyisocyanates include diisocyanates such astrimethylene diisocyatnate, tetramethylene diisocyanate, hexamethylenediisocyanate, pentamethylene diisocyanate, 1,2-propylene diisocyanate,1,2-butylene diisocyanate, 2,3-butylene diisocyanate, 1,3-butylenediisocyanate, 2,4,4- or 2,2,4-trimethylhexamethylene diisocyanate, and2,6-diisocyanatemethylcaproate; and polyisocyanates such as lysine estertriisocyanate, 1,4,8-triisocyanateoctane, 1,6,11-triisocyanateundecane,1,8-diisocyanate-4-isocyanatemethyloctane, 1,3,6-triisocyanatehexane,and 2,5,7-trimethyl-1,8-isocyanate-5-isocyanatemethyloctane.

Moreover, derivatives from the above polyisocyanates can be used.Examples of the derivatives include a dimer, a trimer, biuret,allophanate, carbodiimide, polymethylenepolyphenyl polyisocyanate(referred to as crude MDI or polymeric MDI), crude TDI, and an adduct ofan isocyanate compound and a polyol with a low molecular weight.

While several polyisocyanates, including diisocyanates, have beendisclosed, it must be noted that monoisocyanates may also be employed,provided that it contains a radiation-curable functional group. Anexample of a monoisocyanate comprising a radiation-curable group ismeta-isopropenyl-α,α-dimethyl isocyanate.

“(Meth)acrylate” means acrylate, methacrylate, or a mixture thereof.

The reaction product of polyol and polyisocyanate may be reacted withone or more hydroxy-functional (meth)acrylates. Examples of thehydroxy-functional (meth)acrylates include 2-hydroxyethyl(meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-hydroxybutyl(meth)acrylate, 4-hydroxybutyl (meth)acrylate, pentanediolmono(meth)acrylate, 2-hydroxy-3-phenyloxypropyl (meth)acrylate,2-hydroxyalkyl(meth)acryloyl phosphate, 4-hydroxycyclohexyl(meth)acrylate, cyclohexanedimethanol mono(meth)acrylate, neopentylglycol mono(meth)acrylate, trimethylolpropane di(meth)acrylate, andpentaerythritol tri(meth)acrylate. Additional examples include compoundswhich are obtainable by an addition reaction of a glycidylgroup-containing compound and a (meth)acrylic acid, such as alkylglycidyl ether and glycidyl (meth)acrylate. The above hydroxylgroup-containing (meth)acrylates may be used alone or in combination oftwo or more.

The molecular weight range of radiation-curable oligomers is notparticularly limited, but preferably varies from 5,000 to 25,000 MWbased upon the specific requirements for properties of the primary,secondary or tertiary coating in accordance with the present invention.

Any suitable free radical photoinitiator may be included in theradiation-curable composition. Suitable free radical-typephotoinitiators include, for example, an acyl phosphine oxidephotoinitiator, more specifically, a benzoyl diaryl phosphine oxidephotoinitiator. An example of suitable benzoyl diaryl phosphine oxidephotoinitiators include: 2,4,6-trimethylbenzoyldiphenyl-phosphine oxide(LUCERIN TPO available from BASF). Further examples of free radical-typephotoinitiators include: hydroxycyclohexylphenylketone;hydroxymethylphenylpropanone; dimethoxyphenylacetophenone;2-methyl-1-[4-(methyl thio)-phenyl]-2-morpholinopropanone-1;1-(4-isopropylphenyl)-2-hydroxy-2-methylpropan-1-one;1-(4-dodecyl-phenyl)-2-hydroxy-2-methylpropan-1-one;4-(2-hydroxyethoxy)phenyl-2(2-hydroxy-2-propyl)-ketone; diethoxyphenylacetophenone; 2,4,6-trimethylbenzoyl diphenylphosphone; a mixture of(2,6-dimethoxy benzoyl)-2,4,4-trimethylpentylphosphineoxide and2-hydroxy-2-methyl-1-phenyl-propane-1-one; and mixtures of theforegoing. Many of these are sold under the names IRGACURE® and DAROCUR®and are available from Ciba Additives.

The free radical photoinitiator may be a mixture of phosphine oxidephotoinitiators, an example of which is DAROCUR 4265 available from CibaAdditives. This particular photoiniator is a 50:50 weight percentmixture of diphenyl-2,4,6-trimethyl benzoly phosphine oxide and2-hydroxy-2-methyl-1-phenylpropan-1-one. Another is IRGACURE 1700 (alsofrom Ciba Additives), a blend of bis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide and2-hydroxy-2-methyl-1-phenyl-propane-1-one.

The free radical-type photoinitiator may be used in an amount of 10% orless by weight, for example, about 0.25 to about 6% by weight, e.g.,about 4% by weight based upon the total weight of the composition.

Adequate curing of the present compositions is promoted by the presenceof one or more reactive diluents. The reactive diluent may also functionas a solvent, such as, for example, a solvent for the urethane acrylateoligomer. The use of the reactive diluent(s) allows the formulator toadjust the viscosity and thereby improve processability. In other words,the reactive diluent prevents the viscosity of the composition frombecoming too viscous or inflexible so as to ensure that the compositionwill remain suitable for its applications, including, for example, as aprimary or secondary optical fiber coating.

The mono- or di-functional reactive diluent(s) may, for example, be alower molecular weight, liquid (meth)acrylate-functional compoundincluding the following di(meth)acrylates and monofunctional(meth)acrylates: tridecyl acrylate, 1,6-hexanediol diacrylate,1,4-butanediol diacrylate, ethylene glycol diacrylate, diethylene glycoldiacrylate, tetraethylene glycol diacrylate, tripropylene glycoldiacrylate, neopentyl glycol diacrylate, 1,4-butanediol dimethacrylate,poly(butanediol) diacrylate, tetrathylene glycol dimethacrylate,1,3-butylene glycol diacrylate, tetraethylene glycol diacrylate,triisopropylene glycol diacrylate, triisopropylene glycol diacrylate,ethoxylated bisphenol-A diacrylate, and tetrahydrofurfuryl acrylate(THFA). Another example of a reactive diluent is N-vinyl caprolactam.Further examples are the commercially available products from Sartomer,SR 489, a tridecyl acrylate and SR 506, an isobornyl acrylate.

The present radiation-curable compositions may be free of non-reactivediluents, such as water or organic solvents, which lack ethylenicunsaturation.

In the case where the radiation-curable composition is to be used as aprimary coating composition for optical fibers, the radiation-curablecomposition may include an adhesion promoter. Examples of adhesionpromoters include acid functional materials and organofunctionalsilanes. For example, the organofunctional silane may be anamino-functional silane, an acrylamido-functional silane, amercapto-functional silane, an allyl-functional silane, avinyl-functional silane, a methylacrylate-functional silane, and anacrylate-functional silane. The organofunctional silane may bemercaptoalkyl trialkoxyl silane, a methacryloxylalkyl trialkoxy silane,an aminoalkyl trialkoxyl silane, a vinyl trialkoxyl silane,3-aminopropyl triethoxy silane, 3-methacryloxy-propyltrimethoxy silane,gamma-mercaptopropyl trimethoxy silane, gama-mercaptopropyl(gamma-mercaptopropyl)triethoxy silane, beta-(3,4-epoxycyclohexyl) ethyltrimethoxy silane, gamma-glycidoxypropyl trimethoxy silane,3-vinylthiopropyl trimethoxy silane, vinyl-tris-(beta-methoxyethoxy)silane, vinyl triacetoxy silane, and mixtures thereof. A particulartrialkoxysilane adhesion promoter is UCT 7840KG from United ChemicalTechnologies. A further adhesion promoter is KBM 803, a3-(trimethoxysilyl)propyl thiol from Shin-Etsu Chemical Co., Ltd.

The adhesion promoter, if used, may be present in the primary coatingcomposition in an amount of from about 0.1 to about 10% by weight, forexample, from about 0.1 to about 3% by weight, and, e.g., from about 1%by weight, based upon the total weight of the composition.

Other components that may be utilized in the radiation-curablecomposition include pigments, such as TiO₂, antioxidants, such as IONOLavailable from Aldrich, which is a 2,4,6-tri-tert-butyl-4-methylphenol;flow control agents such as BYK331, a polysiloxane available fromBYK-Chemie USA; sensitizers such as thioxanthone orisopropylthioxanthone (ITX) and their derivatives; stabilizers andwetting agents. Suitable amounts are known to those of ordinary skill inthe art.

In a preferred embodiment of the invention, a radiation-curable monomeror oligomer containing a chromophore moiety(ies) is produced by a methodthat comprises the step of preparing a dye concentrate, or masterbatch.The dye concentrate may comprise a solvent and a chromophore-containingcompound according to the invention, e.g., a radiation-curable monomeror oligomer containing a chromophore molecule according to theinvention. In a particularly preferred embodiment, the solvent acts asboth a solvent and reactive diluent. In a most preferred embodiment, thesolvent that acts as both a solvent and a reactive diluent istetrahydrofurfuryl acrylate (THFA).

Specifically, the chromophore-containing compounds comprising aradiation-curable functional group, or the chromophore-containingcompounds comprising functional groups that react to form theradiation-curable monomers or oligomers containing chromophore moietiesof the present invention, may be prepared as a liquid or powder. Forexample, a so-called “direct-acrylated” chromophore-containing compoundmay exist in liquid form. This type of compound may be used, withoutfurther manipulation, in conjunction with the other components, e.g.,the monomers and oligomers that do not contain a chromophore, thephotoinitiator, reactive diluent, etc., to provide the colored,radiation-curable coatings, colorants, inks or printing compositions ofthe present invention.

In the case where the chromophore-containing compound is in powder form,however, it must be dissolved into solution before it can be used toform a colored, radiation-curable composition according to theinvention, regardless of whether the compound already contains, or hasyet to be provided with, radiation-curable functionality. For example,before (or as) a powder of a chromophore-containing dye that is lackingradiation-curable functionality is reacted with, e.g., a polyisocyanate,and end-capped with one or more radiation-curable groups, e.g., groupscontaining ethylenic unsaturation, the compound must be dissolved intosolution.

After extensive research, the present inventors have found that apowdered, chromophore-containing compound may be most suitably dissolvedinto solution by employing THFA as a combination solvent and reactivediluent. The use of THFA in this regard provides several advantages. Forexample, THFA is photocurable. Therefore, THFA does not need to beremoved from the solution before the solution can be added to thecoating composition. When other solvents, such as tetrahydrofuran (THF),are used to dissolve the chromophore-containing compounds into solution,any excess solvent must be removed from the solution before the solutioncan be added to the coating composition. Otherwise, undesirableproperties may result in the coating, such as the formation of bubbles.As another example of the advantage of using THFA, it is noted thatchromophore-containing compounds demonstrated increased solubility inTHFA in comparison to their solubility in other acrylate-containingcompounds.

Accordingly, in one method for providing a dye concentrate, anisocyanate, e.g., a diisocyanate, is reacted in THFA with at least onecompound having at least one isocyanate-reactive group, such as —OH,—NH₂ and —SH, wherein at least a portion of the compound includes achromophore, such as an anthraquinone, methine or azo chromophore.

The chromophore-containing compound may be charged to a reactorcontaining an isocyanate, a catalyst, and THFA at a rate sufficient toprevent the saturation of the solution with the chromophore-containingcompound. For example, the chromophore-containing compound may becharged to the reactor over a period of from about 30 to 75 minutes,preferably 60 minutes, for a reactor maintained at a temperature of fromabout 40° C. to about 60° C., preferably about 50° C. The isocyanate maybe present in a stoichiometric amount, e.g., the isocyanate may bepresent in an amount of 2 equivalents of diisocyanate per equivalent ofchromophore-containing compound. The catalyst may be any suitablecatalyst, such as, for example, dibutyl tin dilaurate. Once thechromophore-containing compound has been charged to the reactor, thereaction is allowed to proceed for, for example, a period of from 120 to240 minutes, preferably about 180 minutes, while the temperature ismaintained at 50° C. The isocyanate-capped, chromophore-containingcompound is provided with one or more radiation-curable groups byreducing the temperature to, and then maintaining the temperature at,from about 30° C. to about 50° C., preferably about 40° C., while aradiation-curable compound, including both (i) an isocyanate-reactivefunctionality and (ii) a radiation-curable functionality, such asethylenic unsaturation, e.g., an acrylate monomer, is charged to thereactor. Preferably, an inhibitor is also added to the reactionsolution. The reaction is monitored to completion by measuring theisocyanate peaks at 2270 cm⁻¹ by FTIR, a procedure that is well-known inthe art.

After completion, there is provided a dye concentrate, or masterbatch,comprising the solvent and the radiation-curable, chromophore-containingmonomers and/or oligomers. In a preferred embodiment, theradiation-curable, chromophore-containing monomers and/or oligomers arepresent in the dye concentrate in an amount that provides an amount ofchromophore moiety that is greater than 5 wt %, preferably greater than10 wt %, e.g., from about 10 wt % to about 35 wt %, wherein theparticular wt % of the chromophore moiety is calculated by dividing thetotal weight of the total amount of chromophore moieties within theradiation-curable, chromophore-containing monomers and/or oligomers bythe total weight of the dye concentrate (i.e., the amount of, e.g., 15wt %, chromophore moiety does not include the weight of, e.g., anyurethane or acrylate that may be present).

The preparation of a dye concentrate, or masterbatch, provides increasedversatility that enables the radiation-curable, chromophore-containingmonomers and/or oligomers contained in the dye concentrate to be morereadily employed in a wide variety of applications.

For example, the various components of the present invention, includingthe dye concentrate or masterbatch, may be mixed or blended together,using any known equipment, to provide a colored, radiation-curablecoating composition, and an optical fiber may be coated with the coatingcomposition by any known optical fiber production technique. In oneembodiment, a radiation-curable coating composition for providing asecondary coating on an optical fiber will comprise less than 20 wt %,for example, less than 15 wt %, preferably less than 10 wt %, morepreferably less than 5 wt %, e.g., from 0.1 wt % to 10 wt %, of the dyeconcentrate, based on the entire weight of the radiation-curablecomposition. Of course, radiation-curable coating compositions may beprepared that will provide a primary, tertiary, or even single coatingon an optical fiber, and the amount of dye concentrate may bespecifically tailored to the particular end-use application. Likewise, aradiation-curable composition may be provided that will provide acoating on a plurality of optical fibers arranged in an array, or on anoptical fiber ribbon, and again the amount of dye concentrate may bespecifically tailored to the particular end-use application.

The techniques may involve a draw tower in which a preformed glass rodis heated to produce a thin fiber of glass. The fiber is pulledvertically through the draw tower and, along the way, the fiber passesthrough one or more coating stations at which various coatings areapplied and cured in-line to the newly drawn fiber. The coating stationsmay each contain a die having an exit orifice that is sized to apply theparticular coating to the fiber in a desired thickness. Monitoring andmeasuring devices may be provided near each station to ensure that thecoating applied at that station is coated concentrically and to thedesired diameter. Examples of optical fiber coating techniques includethe methods disclosed in U.S. Pat. Nos. 4,351,657, 4,512,281, 4,531,959,4,539,219, 4,792,347, and 4,867,775.

Alternatively, compositions comprising the dye concentrate, ormasterbatch, may be formulated to serve as a colored coating or colorantpackage for a wide variety of other substrates, including, for example,glass, plastic, ceramic, metal, textiles, electronics and wood.Compositions comprising the dye concentrate, or masterbatch, may beemployed as a coating or colorant package in the printing and inkingindustries, when it is desired to replace traditional pigments with dyematerials in a radiation-curable, e.g., uv-curable, vehicle. As seen inthe optical fiber applications, other components of the inks or colorantpackages may include other radiation-curable monomers or multifunctionalradiation-curable materials, photoinitiator(s), stabilizer(s),surfactant(s), etc. in order to adjust viscosity and flowcharacteristics for the desired application.

The inks, coatings, or colorant packages may be applied to substratesother than optical fibers by a number of methods, including printingmethods, such as gravure printing, ink jet printing, etc. In oneembodiment, a radiation-curable ink or colorant package will compriseless than 60 wt %, preferably less than 40 wt %, e.g., from 0.1 wt % to35 wt %, of the dye concentrate, based on the entire weight of theradiation-curable composition.

After the substrate is coated with the radiation-curable composition,the composition may be cured by exposure to a sufficient curing amountof UV irradiation. For example, the coated fiber may be exposed to UVirradiation at a rate of from about 5 to 1000 mJ/cm².

To provide a further detailed description of the invention, severalexamples are provided. Specifically, several synthesis examples forforming colored radiation-curable compounds suitable for use in aradiation-curable composition for coating optical fibers and for formingoptical fiber ribbon matrices are provided hereinafter. Examples ofradiation-curable compositions containing the colored compounds are alsoprovided. Finally, example preparations of dye concentrates areprovided, wherein the dye concentrates can then be applied to the widevariety of applications noted herein above.

EXAMPLE 1 Yellow Oligomer

202.89 g of Milliken REACTINT™ dye yellow X15 was added dropwise to amixture of 67.44 g isophorone diisocyanate (IPDI) and dibutyltindilaurate that had been heated to 40° C. Care was taken that theexothermic reaction did not heat above 45° C. by controlling theaddition rate. The total time taken for addition was two hours. Afterthe last addition of IPDI, 200 g of 1,6 hexanediol diacrylate (HDODA)was added as a reactive diluent to lower viscosity along with 4.4 g ofinhibitor 2,6-Di-tert-butyl-4-methylphenol. This mixture was maintainedat 40° C. for two hours before addition of 35.24 g 2-hydroxyethylacrylate (HEA) dropwise with the temperature maintained below 50° C. bycontrolling the rate of addition of HEA. One hour after addition, therewas no detectible isocyanate peak at 2270 cm⁻¹ as observed by FTIR. Theresulting urethane acrylate oligomeric reaction product has a yellowcolor.

EXAMPLE 2 Blue Oligomer

152.09 g of Milliken REACTINT™ dye blue X3LV was added dropwise to amixture of 101.13 g isophorone diisocyanate (IPDI) and 2.98 g dibutyltindilaurate that had been heated to 40° C. Care was taken that theexothermic reaction did not heat above 45° C. by controlling theaddition rate. The total time taken for addition was two hours. Afterthe last addition of IPDI, 200 g of 1,6 hexanediol diacrylate (HDODA)was added as a reactive diluent to lower viscosity along with 2.03 g ofinhibitor 2,6-di-tert-butyl-4-methylphenol. This mixture was maintainedat 40° C. for two hours before addition of 52.96 g 2 -hydroxyethylacrylate (HEA) dropwise with the temperature maintained below 50° C. bycontrolling the rate of addition of HEA. Two hours after addition, therewas no detectible isocyanate peak at 2270 cm⁻¹ as observed by FTIR. Theresulting urethane acrylate oligomer reaction product has a blue color.

EXAMPLE 3 Black Oligomer

226.67 g of Milliken REACTINT™ dye black X95AB was added dropwise to amixture of 93.30 g isophorone diisocyanate (IPDI) and 2.74 g dibutyltindilaurate that had been heated to 40° C. Care was taken that theexothermic reaction did not heat above 45° C. by controlling theaddition rate. The total time taken for addition was about two hours.After the last addition of IPDI, 200 g of tetrahydrafuran (THF) solventwas added as a reactive diluent to lower viscosity along with 2.38 g ofinhibitor 2,6-di-tert-butyl-4-methylphenol. This mixture was maintainedat 40° C. for two hours before addition of 48.78 g 2-hydroxyethylacrylate (HEA) dropwise with the temperature maintained below 50° C. bycontrolling the rate of addition of HEA. Two hours after addition, therewas no detectible isocyanate peak at 2270 cm⁻¹ as observed by FTIR. TheTHF solvent was then removed via rotovap vacuum technique at roomtemperature over a 10 h period until a weight equal to the originalinputs (minus the solvent) was reached. The resulting urethane acrylateoligomer reaction product has a black color.

Several liquid coating compositions employing the coloredradiation-curable oligomers are described hereinafter.

EXAMPLE 4 Yellow-Colored Optical Fiber Outer Coating Composition

A yellow ultraviolet radiation-curable coating composition for providinga colored outer coating was made by combining 60 weight percent EBECRYL™4827, which is an aromatic urethane diacrylate oligomer having amolecular weight of about 1500 sold by UCB Chemicals, 30 weight percenttrimethylolpropane trimethacrylate (TMPTA) sold by UCB Chemicals, whichis a reactive diluent, 6 weight percent of the yellow colored urethaneacrylate oligomer reaction product of the synthesis described in Example1 and about 4 weight percent of DAROCUR™ 4268 which is a photoinitiator.The coating composition was applied on an inner coating layer and curedby exposing the composition to ultraviolet radiation in a suitablewavelength range and intensity to form a yellow-colored outer protectivepolymeric coating.

EXAMPLE 5 Blue-Colored Optical Fiber Inner Coating Composition

A blue ultraviolet radiation-curable coating composition for providing acolored inner coating was made by combining 60 weight percent EBECRYL™230, which is a high molecular weight aliphatic urethane diacrylateoligomer (bulk oligomer) sold by UCB Chemicals, 29 weight percentbeta-carboxyethyl acrylate (13-CEA) sold by UCB Chemicals, which is amonofunctional reactive diluent, 6 weight percent of the blue coloredurethane acrylate oligomer reaction product of the synthesis describedin Example 2 and about 5 weight percent of DAROCUR® 4265, which is aphotoinitiator. The coating composition was applied on the cladding ofan optical fiber and cured by exposure to ultraviolet radiation in asuitable wavelength range and intensity to form a blue-colored innerprotective coating.

EXAMPLE 6 Blue-Colored Optical Fiber Outer Coating Composition

A blue ultraviolet radiation-curable coating composition for providing acolored outer coating was made by combining 60 weight percent EBECRYL™4827 (bulk oligomer), 30 weight percent TMPTA (reactive diluent), 6weight percent of the blue-colored urethane acrylate oligomer reactionproduct of the synthesis described in Example 2 and about 4 weightpercent of DAROCUR™ 4268. The coating composition was applied to theinner coating of an optical fiber to form a blue-colored outerprotective polymeric coating after curing by exposure to ultravioletradiation in a suitable wavelength range.

EXAMPLE 7 Blue-Colored Ink (Tertiary) Coating Composition

A blue ultraviolet radiation-curable coating composition for providing acolored tertiary coating was made by combining 25 weight percentEBECRYL™ 4866, which is an aliphatic urethane triacrylate diluted with30 weight percent tripropylene glycol diacrylate (TRPGDA) sold by UCBChemicals, 25 weight percent TMPTA (a reactive diluent), 35 weightpercent of the blue-colored urethane acrylate oligomer reaction productof the synthesis described in Example 2, 10 weight percent hexanedioldiacrylate (HDODA) (a reactive diluent) and about 5 weight percent ofDAROCUR™ 4268. The coating composition was applied over the outercoating of an optical fiber and cured by exposure to ultravioletradiation in a suitable wavelength range to form a blue-colored tertiaryprotective polymeric coating.

EXAMPLE 8 Blue Urethane Acrylate

11.16 g of isophorone diisocyanate and 0.35 g of dibutyltin dilauratewas heated to 50° C. 16.34 g of 1,5-bis ((2,2-dimethyl-3-hydroxypropyl)amino)-4,8-bis((4-methylphenyl)thio) anthraquinone was mixed with THF toget the anthracenedione into solution and added slowly to the reaction.The reaction temperature was maintained at 50° C. for three hours. Thetemperature was reduced to 40° C. and 0.25 g of2,6-di-tert-butyl-4-methylphenol and 30 g of 1,6 hexanediol diacrylatewas added to the reaction. 5.819 g of 2-hydroxyethyl acrylate was thenadded dropwise. The reaction was run to completion by measuring theisocyanate peak at 2270 cm⁻¹ by FTIR. The THF was evaporated off of themixture. The resulting urethane acrylate compound was blue in color.

EXAMPLE 9 Blue-Colored Optical Fiber Outer Coating

A blue ultraviolet radiation-curable coating composition for providing acolored outer coating was made by combining 65 weight percent of EBECRYL4827, which is a urethane acrylate oligomer (bulk oligomer), 30 weightpercent tripropylene glycol diacrylate (TPGDA), which is a reactivediluent, 1 percent of the blue-colored urethane acrylate reactionproduct of the synthesis described in Example 8 and about 4 percent ofDAROCUR™ 4268 which is a photoinitiator. The coating composition wasapplied to an inner coating layer and cured by exposing the compositionto ultraviolet radiation at a suitable wavelength range to form ablue-colored outer protective polymeric coating.

EXAMPLE 10 Blue-Colored Optical Fiber Inner Coating

A blue ultraviolet radiation-curable coating composition for providing acolored inner coating was made by combining 65 weight percent ofEBECRYL™ 230, which is a urethane acrylate oligomer, 29 weight percentβ-CEA monofunctional reactive diluent, 1 percent of the blue-coloredurethane acrylate reaction product of the synthesis described in Example8 and about 5 weight percent DAROCUR™ 4265, which is a photoinitiator.The coating composition was applied to the cladding of an optical fiberand cured by exposure to ultraviolet radiation in a suitable wavelengthrange to form a blue colored inner protective fiber coating.

Colored Optical Fiber Ribbon

Referring to FIG. 2, there is shown a typical splittable optical fiberribbon 22 containing two planar arrays 24 a, 24 b of optical fibers 21.Each of the arrays of optical fibers are enveloped by a primary matrix26 a, 26 b that hold the fiber arrays together. Both primary matrices 26a, 26 b are enveloped by a secondary matrix 28. The primary matrices 26a, 26 b, the secondary matrix 28 or both may be colored in accordancewith the present invention. An example of a colored matrix is describedbelow.

EXAMPLE 11 Blue Ribbon Matrix

A composition for forming a blue-colored optical fiber ribbon matrix wasmade by combining 6 weight percent of the blue oligomer reaction productdescribed in Example 2, 60 weight percent EBECRYL™ 4866 trifunctionaloligomer (bulk oligomer), 30 weight percent TMPTA (reactive diluent) and4 weight percent DAROCUR™ 4268 photoinitiator. The resulting compositionwas applied over a planar array of optical fibers using ordinaryapplication methods with a die or an applicator. The composition wascured by exposure to ultraviolet radiation in a suitable wavelengthrange to form a blue-colored matrix over the planar array of opticalfibers.

EXAMPLE 12 Yellow Reactive Dye Color Concentrate

A reactive dye color concentrate containing a functionalized yellow dyecompound was prepared according to the procedure below:

2 equivalents of isophorone diisocyanate (IPDI), 0.01 mol dibutyl tindilaurate, and tetrahydrofurfuryl acrylate (amount sufficient toultimately give 15% by weight chromophore moiety concentration in thecolor concentrate) were charged to a reactor, stirred at 650 rpm andheated to 50° C. One (1) equivalent of2,2′-((9,10-dihydro-9,10-dioxo-1,5-anthracenediyl)bis(thio))bis-benzoicacid, 2-hydroxyethyl ester anthraquinone yellow dye was then addedslowly to the reactor over a 1-hour period. The tetrahydrofurfurylacrylate monomer served as a solvent, allowing the dye to be dissolvedinto solution and to react with the diisocyanate forming anisocyanate-containing, dye-containing compound. The dye was added slowlyto the reactor so as not to saturate the solution, which wouldessentially stop the urethanization reaction.

After completion of the addition of the dye, the reaction was allowed toproceed for a 3-hour period while the temperature is maintained at 50C.After the 3-hour reaction period, the temperature was reduced to 40° C.and 0.02 mol of 2.6-di-tert-butyl-4-methylphenol (inhibitor) was addedto the reaction solution. One (1) equivalent of 2-hydroxyethyl acrylatewas added slowly and reacted with the isocyanate of theisocyanate-containing, dye-containing compound. The temperature wasmaintained at 40° C. and the mixture was stirred for 2 hours. Thereaction was monitored to completion by measuring the isocyanate peak at2270 cm⁻¹ by FTIR. At the end of the two-hour reaction period, there wasno free isocyanate present in the mixture as measured by FTIR.

The resulting yellow color concentrate, which contained 15% by weight ofchromophore moiety based on the total weight of the color concentrate(i.e., the amount of 15 wt % chromophore moiety does not include theweight of the urethane or acrylate), was filtered through a 1-micronabsolute filter. There were no solids recovered from the filter.

EXAMPLE 13 Orange Reactive Dye Color Concentrate

A reactive dye color concentrate containing a functionalized orange dyecompound was prepared according to the procedure below:

2 equivalents of isophorone diisocyanate (IPDI), 0.01 mol dibutyl tindilaurate, and tetrahydrofurfuryl acrylate (amount sufficient toultimately give 15% by weight chromophore moiety concentration in thecolor concentrate) were charged to a reactor, stirred at 650 rpm andheated to 50° C. 1 equivalent of 2,5-bis-(phenylamino)terephthalic acidbis-(2-hydroxyethyl) ester anthraquinone orange dye was then addedslowly to the reactor over a 1-hour period. The tetrahydrofurfurylacrylate monomer served as a solvent allowing the dye to be dissolvedinto solution and to react with the diisocyanate forming anisocyanate-containing, dye-containing compound. The dye was added slowlyto the reactor so as not to saturate the solution, which wouldessentially stop the urethanization reaction.

After completion of the addition of the dye, the reaction was allowed toproceed for a 3-hour period while the temperature was maintained at 50°C. After the 3-hour reaction period, the temperature was reduced to 40°C. and 0.02 mol of 2.6-Di-tert-butyl-4 -O methylphenol (inhibitor) wasadded to the reaction solution. One (1) equivalent of 2 -hydroxyethylacrylate was added slowly and reacted with the isocyanate of theisocyanate-containing, dye-containing compound. The temperature wasmaintained at 40° C. and the mixture was allowed to stir for 2 hours.The reaction was monitored to completion by measuring the isocyanatepeak at 2270 cm⁻¹ by FTIR. At the end of the two-hour reaction period,there was no free isocyanate present in the mixture as measured by FTIR.

The resulting orange color concentrate, which contained 15% by weight ofchromophore moiety based on the total weight of the color concentrate(i.e., the amount of 15 wt % chromophore moiety does not include theweight of the urethane or acrylate), was filtered through a 1-micronabsolute filter. There were no solids recovered from the filter.

EXAMPLE 14 Red Reactive Dye Color Concentrate

The reactive dye color concentrate containing a functionalized red dyecompound was prepared according to the procedure below:

2 equivalents of isophorone diisocyanate (IPDI), 0.01 mol dibutyl tindilaurate, and tetrahydrofurfuryl acrylate (amount sufficient toultimately give 15% by weight chromophore moiety concentration in thecolor concentrate) were charged to a reactor, stirred at 650 rpm andheated to 50° C. One (1) equivalent of1,5-bis-{(3-hydroxypropyl)amino}-9,10-anthracenedione red anthraquinonedye was then added slowly to the reactor over a 1-hour period. Thetetrahydrofurfuryl acrylate monomer served as a solvent allowing the dyeto be dissolved into solution and to react with the diisocyanate formingan isocyanate-containing, dye-containing compound. The dye was addedslowly to the reactor so as not to saturate the solution, which wouldessentially stop the urethanization reaction.

After completion of the addition of the dye, the reaction was allowed toproceed for a 3-hour period while the temperature was maintained at 50°C. After the 3-hour reaction period, the temperature was reduced to 40°C. and 0.02 mol of 2.6-Di-tert-butyl-4-methylphenol (inhibitor) wasadded to the reaction solution. One (1) equivalent of 2-hydroxyethylacrylate was added slowly and reacted with the isocyanate of theisocyanate-containing, dye-containing compound. The temperature wasmaintained at 40° C. and the mixture was stirred for 2 hours. Thereaction was monitored to completion by measuring the isocyanate peak at2270 cm⁻¹ by FTIR. At the end of the two-hour reaction period, there wasno free isocyanate present in the mixture as measured by FTIR.

The resulting red color concentrate, which contained 15% by weight ofchromophore moiety based on the total weight of the color concentrate(i.e., the amount of 15 wt % chromophore moiety does not include theweight of the urethane or acrylate), was filtered through a 1-micronabsolute filter. There were no solids recovered from the filter.

COMPARATIVE EXAMPLE 1 Yellow Reactive Dye Color Concentrate

A reactive dye color concentrate containing a functionalized yellow dyecompound was prepared according to the procedure below:

Two (2) equivalents of isophorone diisocyanate (IPDI), 0.01 mol dibutyltin dilaurate, and tripropylene glycol diacrylate (TPGDA) (amountsufficient to ultimately give 15% by weight chromophore moietyconcentration in the color concentrate) were charged to a reactor,stirred at 650 rpm and heated to 50° C. One (1) equivalent of2,2′-((9,10-dihydro-9,10-dioxo-1,5-anthracenediyl)bis(thio))bis-benzoicacid, 2 hydroxyethyl ester anthraquinone yellow dye was then addedslowly to the reactor over a 1-hour period. The tripropylene glycoldiacrylate monomer served as a solvent allowing the dye to be dissolvedinto solution and to react with the diisocyanate forming anisocyanate-containing, dye-containing compound. The dye was added slowlyto the reactor so as not to saturate the solution, which wouldessentially stop the urethanization reaction.

After completion of the addition of the dye, the reaction was allowed toproceed for a 3-hour period while the temperature was maintained at 50°C. After the 3-hour reaction period, the temperature was reduced to 40°C. and 0.02 mol of 2.6-Di-tert-butyl-4-methylphenol (inhibitor) wasadded to the reaction solution. One (1) equivalent of 2-hydroxyethylacrylate was added slowly and reacted with the isocyanate of theisocyanate-containing, dye-containing compound. The temperature wasmaintained at 40° C. and the mixture was allowed to stir for 2 hours.The reaction was monitored to completion by measuring the isocyanatepeak at 2270 cm⁻¹ by FTIR. At the end of the two-hour reaction period,there were approximately 0.5 equivalents of free isocyanate present.

The resulting yellow color concentrate was filtered through a 1.2-micronabsolute filter. Approximately 0.6 equivalents of solid diol dye(unreacted) was recovered from the filter. The reaction was unsuccessfuldue to lack of solubility of the yellow anthraquinone dye in thereaction mixture when using monomer TPGDA.

COMPARATIVE EXAMPLE 2 Orange Reactive Dye Color Concentrate

A reactive dye color concentrate containing a functionalized orange dyecompound was prepared according to the procedure below:

2 equivalents of isophorone diisocyanate (IPDI), 0.01 mol dibutyl tindilaurate, and tripropylene glycol diacrylate (TPGDA) (amount sufficientto ultimately give 15% by weight chromophore moiety concentration in thecolor concentrate) were charged to a reactor, stirred at 650 rpm andheated to 50° C. One (1) equivalent of 2,5-bis-(phenylamino)terephthalicacid bis-(2-hydroxyethyl) ester anthraquinone orange dye was then addedslowly to the reactor over a 1-hour period. The tripropylene glycoldiacrylate monomer served as a solvent allowing the dye to be dissolvedinto solution and to react with the diisocyanate forming anisocyanate-containing, dye-containing compound. The dye was added slowlyto the reactor so as not to saturate the solution, which wouldessentially stop the urethanization reaction.

After completion of the addition of the dye, the reaction was allowed toproceed for a 3-hour period while the temperature was maintained at 50°C. After the 3-hour reaction period, the temperature was reduced to 40°C. and 0.02 mol of 2.6-Di-tert-butyl-4-methylphenol (inhibitor) is addedto the reaction solution. One (1) equivalent of 2-hydroxyethyl acrylatewas added slowly and reacted with the isocyanate of theisocyanate-containing, dye-containing compound. The temperature wasmaintained at 40° C. and the mixture was allowed to stir for 2 hours.The reaction was monitored to completion by measuring the isocyanatepeak at 2270 cm⁻¹ by FTIR. At the end of the two-hour reaction period,there were approximately 0.2 equivalents of free isocyanate present asmeasured by FTIR.

The resulting orange color concentrate was filtered through a 1.2-micronabsolute filter. Approximately 0.2 equivalents of unreacted solid orangeanthraquinone dye were recovered from the filter. The reaction wasunsuccessful due to limited solubility of the orange diol dye in thereaction mixture when using monomer TPGDA.

COMPARATIVE EXAMPLE 3 Red Reactive Dye Color Concentrate

A reactive dye color concentrate containing a functionalized red dyecompound was prepared according to the procedure below:

Two (2) equivalents of isophorone diisocyanate (IPDI), 0.01 mol dibutyltin dilaurate, and tripropylene glycol diacrylate (TPGDA) (amountsufficient to ultimately give 15% by weight chromophore moietyconcentration in the color concentrate) were charged to a reactor,stirred at 650 rpm and heated to 50° C. One (1) equivalent1,5-bis-{(3-hydroxypropyl)amino}-9,10-anthracenedione red anthraquinonedye was then added slowly to the reactor over a 1-hour period. Thetripropylene glycol diacrylate monomer served as a solvent allowing thedye to be dissolved into solution and to react with the diisocyanateforming an isocyanate-containing, dye-containing compound. The dye wasadded slowly to the reactor so as not to saturate the solution, whichwould essentially stop the urethanization reaction.

After completion of the addition of the dye, the reaction was allowed toproceed for a 3-hour period while the temperature was maintained at 50°C. After the 3-hour reaction period, the temperature was reduced to 40°C. and 0.02 mol of 2.6-di-tert-butyl-4-methylphenol (inhibitor) wasadded to the reaction solution. One (1) equivalent of 2-hydroxyethylacrylate was added slowly and reacted with the isocyanate of theisocyanate-containing, dye-containing compound. The temperature wasmaintained at 40° C. and the mixture was allowed to stir for 2 hours.The reaction was monitored to completion by measuring the isocyanatepeak at 2270 cm⁻¹ by FTIR. At the end of the two-hour reaction period,there were approximately 0.8 equivalents of free isocyanate present asmeasured by FTIR.

The resulting red color concentrate was filtered through a 1-micronabsolute filter. Approximately 0.6 equivalents of unreacted solid reddiol dye were recovered from the filter. The reaction was unsuccessfuldue to limited solubility of the red anthraquinone dye in the reactionmixture when using monomer TPGDA.

COMPARATIVE EXAMPLE 4 Yellow Reactive Dye Color Concentrate

A reactive dye color concentrate containing a functionalized yellow dyecompound was prepared according to the procedure below:

Two (2) equivalents of isophorone diisocyanate (IPDI), 0.01 mol dibutyltin dilaurate, and 2-phenoxyethyl acrylate (2-PEA) (amount sufficient toultimately give 15% by weight chromophore moiety concentration in thecolor concentrate) were charged to a reactor, stirred at 650 rpm andheated to 50° C. One (1) equivalent of2,2′-((9,10-dihydro-9,10-dioxo-1,5-anthracenediyl)bis(thio))bis-benzoicacid, 2 hydroxyethyl ester anthraquinone yellow dye was then addedslowly to the reactor over a 1-hour period. The 2-phenoxyethyl acrylatemonomer served as a solvent allowing the dye to be dissolved intosolution and to react with the diisocyanate forming anisocyanate-containing, dye-containing compound. The dye was added slowlyto the reactor so as not to saturate the solution, which wouldessentially stop the urethanization reaction.

After completion of the addition of the dye, the reaction was allowed toproceed for a 3-hour period while the temperature was maintained at 50°C. After the 3-hour reaction period, the temperature was reduced to 40°C. and 0.02 mol of 2.6-Di-tert-butyl-4-methylphenol (inhibitor) wasadded to the reaction solution. One (1) equivalent of 2-hydroxyethylacrylate was added slowly and reacted with the isocyanate of theisocyanate-containing, dye-containing compound. The temperature wasmaintained at 40° C. and the mixture was allowed to stir for 2 hours.The reaction was monitored to completion by measuring the isocyanatepeak at 2270 cm⁻¹ by FTIR. At the end of the two-hour reaction period,there were approximately 0.8 equivalents of free isocyanate present.

The resulting yellow color concentrate was filtered through a 1.2-micronabsolute filter. Approximately 0.5 equivalents of solid diol dye(unreacted) was recovered from the filter. The reaction was unsuccessfuldue to lack of solubility of the yellow anthraquinone dye in thereaction mixture when using monomer 2-PEA.

COMPARATIVE EXAMPLE 5 Orange Reactive Dye Color Concentrate

A reactive dye color concentrate containing a functionalized orange dyecompound was prepared according to the procedure below:

Two (2) equivalents of isophorone diisocyanate (IPDI), 0.01 mol dibutyltin dilaurate, and 2-phenoxyethyl acrylate (2-PEA) (amount sufficient toultimately give 15% by weight chromophore moiety concentration in thecolor concentrate) were charged to a reactor, stirred at 650 rpm andheated to 50° C. One (1) equivalent of 2,5-bis-(phenylamino)terephthalicacid bis-(2-hydroxyethyl) ester anthraquinone orange dye was then addedslowly to the reactor over a 1-hour period. The 2-phenoxyethyl acrylatemonomer served as a solvent allowing the dye to be dissolved intosolution and to react with the diisocyanate forming anisocyanate-containing, dye-containing compound. The dye be added slowlyto the reactor so as not to saturate the solution, which wouldessentially stop the urethanization reaction.

After completion of the addition of the dye, the reaction was allowed toproceed for a 3-hour period while the temperature was maintained at 50°C. After the 3-hour reaction period, the temperature was reduced to 40°C. and 0.02 mol of 2.6-di-tert-butyl-4-methylphenol (inhibitor) wasadded to the reaction solution. One (1) equivalent of 2-hydroxyethylacrylate was added slowly and reacted with the isocyanate of theisocyanate-containing, dye-containing compound. The temperature wasmaintained at 40° C. and the mixture was allowed to stir for 2 hours.The reaction was monitored to completion by measuring the isocyanatepeak at 2270 cm⁻¹ by FTIR. At the end of the two-hour reaction period,there were approximately 0.8 equivalents of free isocyanate present asmeasured by FTIR.

The resulting orange color concentrate was filtered through a 1.2-micronabsolute filter. Approximately 0.7 equivalents of unreacted solid orangeanthraquinone dye were recovered from the filter. The reaction wasunsuccessful due to limited solubility of the orange diol dye in thereaction mixture when using monomer 2-PEA.

COMPARATIVE EXAMPLE 6 Red Reactive Dye Color Concentrate

A reactive dye color concentrate containing a functionalized red dyecompound was prepared according to the procedure below:

Two (2) equivalents of isophorone diisocyanate (IPDI), 0.01 mol dibutyltin dilaurate, and 2-phenoxyethyl acrylate (2-PEA) (amount sufficient toultimately give 15% by weight chromophore moiety concentration in thecolor concentrate) were charged to a reactor, stirred at 650 rpm andheated to 50° C. 1 equivalent1,5-bis-{(3-hydroxypropyl)amino}-9,10-anthracenedione red anthraquinonedye was then added slowly to the reactor over a 1-hour period. The2-phenoxyethyl acrylate monomer served as a solvent allowing the dye tobe dissolved into solution and to react with the diisocyanate forming anisocyanate-containing, dye-containing compound. The dye was added slowlyto the reactor so as not to saturate the solution, which wouldessentially stop the urethanization reaction.

After completion of the addition of the dye, the reaction was allowed toproceed for a 3-hour period while the temperature was maintained at 50°C. After the 3-hour reaction period, the temperature was reduced to 40°C. and 0.02 mol of 2.6 di-tert-butyl-4-methylphenol (inhibitor) wasadded to the reaction solution. One (1) equivalent of 2-hydroxyethylacrylate was added slowly and reacted with the isocyanate of theisocyanate-containing, dye-containing compound. The temperature wasmaintained at 40° C. and the mixture was allowed to stir for 2 hours.The reaction was monitored to completion by measuring the isocyanatepeak at 2270 cm⁻¹ by FTIR. At the end of the two-hour reaction period,there were approximately 0.8 equivalents of free isocyanate present asmeasured by FTIR.

The resulting red color concentrate was filtered through a 1-micronabsolute filter. Approximately 0.6 equivalents of unreacted solid reddiol dye were recovered from the filter. The reaction was unsuccessfuldue to limited solubility of the red anthraquinone dye in the reactionmixture when using monomer 2-PEA.

COMPARATIVE EXAMPLE 7 Yellow Reactive Dye Color Concentrate

A reactive dye color concentrate containing a functionalized yellow dyecompound was prepared according to the procedure below:

Two (2) equivalents of isophorone diisocyanate (IPDI), 0.01 mol dibutyltin dilaurate, and isobornyl acrylate (IBOA) (amount sufficient toultimately give 15% by weight chromophore moiety concentration in thecolor concentrate) were charged to a reactor, stirred at 650 rpm andheated to 50° C. One (1) equivalent of2,2′-((9,10-dihydro-9,10-dioxo-1,5-anthracenediyl)bis(thio))bis-benzoicacid, 2 hydroxyethyl ester anthraquinone yellow dye was then addedslowly to the reactor over a 1-hour period. The isobornyl acrylatemonomer served as a solvent allowing the dye to be dissolved intosolution and to react with the diisocyanate forming anisocyanate-containing, dye-containing compound. The dye was added slowlyto the reactor so as not to saturate the solution, which wouldessentially stop the urethanization reaction.

After completion of the addition of the dye, the reaction was allowed toproceed for a 3-hour period while the temperature was maintained at 50°C. After the 3-hour reaction period, the temperature was reduced to 40°C. and 0.02 mol of 2.6-di-tert-butyl-4-methylphenol (inhibitor) wasadded to the reaction solution. One (1) equivalent of 2-hydroxyethylacrylate was added slowly and reacted with the isocyanate of theisocyanate-containing, dye-containing compound. The temperature wasmaintained at 40° C. and the mixture was allowed to stir for 2 hours.The reaction was monitored to completion by measuring the isocyanatepeak at 2270 cm⁻¹ by FTIR. At the end of the two-hour reaction period,there were approximately 0.6 equivalents of free isocyanate present.

The resulting yellow color concentrate was filtered through a 1.2-micronabsolute filter. Approximately 0.6 equivalents of solid diol dye(unreacted) was recovered from the filter. The reaction was unsuccessfuldue to lack of solubility of the yellow anthraquinone dye in thereaction mixture when using monomer IBOA.

COMPARATIVE EXAMPLE 8 Orange Reactive Dye Color Concentrate

A reactive dye color concentrate containing a functionalized orange dyecompound was prepared according to the procedure below:

Two (2) equivalents of isophorone diisocyanate (IPDI), 0.01 mol dibutyltin dilaurate, and isobornyl acrylate (IBOA) (amount sufficient toultimately give 15% by weight chromophore moiety concentration in thecolor concentrate) were charged to a reactor, stirred at 650 rpm andheated to 50° C. One (1) equivalent of 2,5-bis-(phenylamino)terephthalicacid bis-(2-hydroxyethyl) ester anthraquinone orange dye was then addedslowly to the reactor over a 1-hour period. The isobornyl acrylatemonomer served as a solvent allowing the dye to be dissolved intosolution and to react with the diisocyanate forming anisocyanate-containing, dye-containing compound. The dye be added slowlyto the reactor so as not to saturate the solution, which wouldessentially stop the urethanization reaction.

After completion of the addition of the dye, the reaction was allowed toproceed for a 3-hour period while the temperature was maintained at 50°C. After the 3-hour reaction period, the temperature was reduced to 40°C. and 0.02 mol of 2.6-di-tert-butyl-4-methylphenol (inhibitor) wasadded to the reaction solution. One (1) equivalent of 2-hydroxyethylacrylate was added slowly and reacted with the isocyanate of theisocyanate-containing, dye-containing compound. The temperature wasmaintained at 40° C. and the mixture was allowed to stir for 2 hours.The reaction was monitored to completion by measuring the isocyanatepeak at 2270 cm⁻¹ by FTIR. At the end of the two-hour reaction period,there were approximately 0.4 equivalents of free isocyanate present asmeasured by FTIR.

The resulting orange color concentrate was filtered through a 1.2-micronabsolute filter. Approximately 0.4 equivalents of unreacted solid orangeanthraquinone dye were recovered from the filter. The reaction wasunsuccessful due to limited solubility of the orange diol dye in thereaction mixture when using monomer IBOA.

COMPARATIVE EXAMPLE 9 Red Reactive Dye Color Concentrate

A reactive dye color concentrate containing a functionalized red dyecompound was prepared according to the procedure below:

Two (2) equivalents of isophorone diisocyanate (IPDI), 0.01 mol dibutyltin dilaurate, and isobornyl acrylate (BOA) (amount sufficient toultimately give 15% by weight chromophore moiety concentration in thecolor concentrate) were charged to a reactor, stirred at 650 rpm andheated to 50° C. One (1) equivalent1,5-bis-{(3-hydroxypropyl)amino}-9,10-anthracenedione red anthraquinonedye was then added slowly to the reactor over a 1-hour period. Theisobornyl acrylate monomer served as a solvent allowing the dye to bedissolved into solution and to react with the diisocyanate forming anisocyanate-containing, dye-containing compound. The dye be added slowlyto the reactor so as not to saturate the solution, which wouldessentially stop the urethanization reaction.

After completion of the addition of the dye, the reaction was allowed toproceed for a 3-hour period while the temperature was maintained at 50°C. After the 3-hour reaction period, the temperature was reduced to 40°C. and 0.02 mol of 2.6-di-tert-butyl-4-methylphenol (inhibitor) wasadded to the reaction solution. One (1) equivalent of 2-hydroxyethylacrylate was added slowly and reacted with the isocyanate of theisocyanate-containing, dye-containing compound. The temperature wasmaintained at 40° C. and the mixture was allowed to stir for 2 hours.The reaction was monitored to completion by measuring the isocyanatepeak at 2270 cm⁻¹ by FTIR. At the end of the two-hour reaction period,there were approximately 0.8 equivalents of free isocyanate present asmeasured by FTIR.

The resulting red color concentrate was filtered through a 1-micronabsolute filter. Approximately 0.7 equivalents of unreacted solid reddiol dye were recovered from the filter. The reaction was unsuccessfuldue to limited solubility of the red anthraquinone dye in the reactionmixture when using monomer IBOA.

The embodiments disclosed herein admirably achieve the objects of thepresent invention; however, it should be appreciated by those skilled inthe art that departures can be made by those skilled in the art withoutdeparting from the spirit and scope of the invention which is limitedonly by the following claims.

1. A telecommunication element having a color identifying coatingthereon, the telecommunication element comprising: an elongatedcommunication transmission medium; and a coating having an identifyingcolor applied on at least a portion of the transmission medium, whereinsaid coating comprises a radiation-cured, crosslinked, polymericnetwork, and wherein the identifying color in the coating is at least inpart provided by at least one chromophore moiety covalently bonded by atleast one covalent bond to said polymeric network.
 2. Thetelecommunications element of claim 1, wherein: (a) the elongatedtransmission medium is selected from the group consisting of (i) anoptical fiber having a core and a cladding surrounding the core, (ii) anoptical fiber having a core, a cladding surrounding the core, and one ormore polymeric coatings on the cladding, (iii) a plurality of opticalfibers arranged in an array, and (iv) an optical fiber ribbon; and (b)the identifying color is thermally stable and light fast.
 3. Thetelecommunications element of claim 1, wherein the identifying color inthe coating is at least in part provided by at least one anthraquinonemoiety covalently bonded by at least one covalent bond to said polymericnetwork.
 4. The telecommunications element of claim 1, wherein theidentifying color in the coating is at least in part provided by atleast one methine moiety covalently bonded by at least one covalent bondto said polymeric network.
 5. The telecommunications element of claim 1,wherein the identifying color in the coating is at least in partprovided by at least one azo moiety covalently bonded by at least onecovalent bond to said polymeric network.
 6. A radiation-curable,chromophore-containing compound comprising at least oneradiation-curable group and at least one chromophore moiety, wherein theradiation-curable, chromophore-containing compound comprises thereaction product of: (a) an isocyanate-containing compound comprising(i) at least one isocyanate group and (ii) the at least one chromophoremoiety, and (b) a radiation-curable compound comprising (i) at least oneisocyanate-reactive functional group and (ii) the at least oneradiation-curable group, wherein the at least one radiation-curablegroup of said radiation-curable, chromophore-containing compound iscovalently bonded to said radiation-curable, chromophore-containingcompound by at least one covalent bond formed by reacting anisocyanate-reactive functional group (i) of said radiation-curablecompound (b) with an isocyanate group (i) of said isocyanate-containingcompound (a), and said isocyanate-containing compound (a) is thereaction product of: (c) a chromophore-containing compound comprising(i) a chromophore moiety and (ii) at least one isocyanate-reactivefunctional group; and (d) a polyisocyanate.
 7. The radiation-curable,chromophore-containing compound of claim 6, wherein the at least oneisocyanate-reactive functional group (i) of said radiation-curablecompound (b) and the at least one isocyanate-reactive functional group(ii) of said chromophore-containing compound (c) are independentlyselected from the group consisting of —OH, —NH₂ and —SH.
 8. Theradiation-curable, chromophore-containing compound of claim 6, whereinthe at least one radiation-curable group (ii) of said radiation-curablecompound (b) comprises ethylenic unsaturation.
 9. The radiation-curable,chromophore-containing compound of claim 8, wherein theethylenically-unsaturated, radiation-curable group (ii) of saidradiation-curable compound (b) comprises a (meth)acrylate.
 10. Theradiation-curable, chromophore-containing compound of claim 6, whereinthe at least one radiation-curable group (ii) of said radiation-curablecompound (b) comprises an epoxy group.
 11. The radiation-curable,chromophore-containing compound of claim 6, wherein the polyisocyanate(d) is a diisocyanate.
 12. The radiation-curable, chromophore-containingcompound of claim 6, wherein the at least one chromophore moiety (i) ofsaid chromophore-containing compound (c) is a methine dye.
 13. Theradiation-curable, chromophore-containing compound of claim 6, whereinthe at least one chromophore moiety (i) of said chromophore-containingcompound (c) is an azo dye.
 14. The radiation-curable,chromophore-containing compound of claim 6, wherein the at least onechromophore moiety (i) of said chromophore-containing compound (c) is ananthraquinone dye.
 15. The radiation-curable, chromophore-containingcompound of claim 14, wherein the anthraquinone dye has the followingformula:

wherein R groups R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸ are eachindependently selected from the group consisting of hydrogen, amino,hydroxy, halogen, nitro, carboxylated alkali metal, sulfated alkalimetal and a hydrocarbyl group optionally containing one or moreheteroatoms, provided that at least two of R groups R¹ through R⁸ haveat least one isocyanate-reactive functional group selected from thegroup consisting of —OH, —NH₂ and —SH, and further wherein adjacent Rgroups from among R¹ through R⁸ can form a ring.
 16. Theradiation-curable, chromophore-containing compound of claim 15, whereinfrom 1 to 3 of said R groups R¹ through R⁸ have the following formula:

wherein R⁹ is hydrogen or an alkyl group having from 1 to about 12carbon atoms, X is —CH₂—, a is an integer from 1 to about 6, Yrepresents polymeric units of hydroxy alkylenes or alkylene oxidemonomers selected from the group consisting of ethylene oxide, propyleneoxide, butylene oxide, cyclohexane oxide, and glycidol, b is either 0 or1, and Z is —OH, —NH₂, or —SH group, and further wherein the remainderof said R groups R¹ through R⁸ are selected from the group consisting ofhydrogen, amino, hydroxy, halogen, nitro, carboxylated alkali metal andsulfated alkali metal.
 17. The radiation-curable, chromophore-containingcompound of claim 15, wherein the anthraquinone dye has the followingformula:

wherein R⁹ and R¹⁰ are independently selected from hydrogen or an alkylgroup having from 1 to about 12 carbon atoms, X is —CH₂—, a and a′independently are integers from 1 to about 6, Y and Y′ are independentlyrepresent polymeric units of hydroxy alkylenes or alkylene oxidemonomers selected from the group consisting of ethylene oxide, propyleneoxide, butylene oxide, cyclohexane oxide, and glycidol, b and b′ areindependently either 0 or 1, and Z and Z′ independently are —OH, —NH₂,or —SH groups.
 18. The radiation-curable, chromophore-containingcompound of claim 17, wherein the anthraquinone dye has the formula:

wherein n, n′, m, m′, p, and p′ independently have a value of from 0 toabout
 40. 19. The radiation-curable, chromophore-containing compound ofclaim 17, wherein the anthraquinone dye has the formula:


20. The radiation-curable, chromophore-containing compound of claim 14,wherein the anthraquinone dye is selected from the group consisting of1,5-bis((3-hydroxy-2,2-dimethylpropyl)amino)-9,10-anthracenedione;2,2′-((9,10-dihydro-9, 10-dioxo-1,5-anthracenediyl)bis(thio))bis-benzoicacid, 2-hydroxyethyl ester, and1,5-bis((2,2-dimethyl-3-hydroxypropyl)amino)-4,8-bis((4-methylphenyl)thio)anthraquinone.
 21. The radiation-curable, chromophore-containingcompound of claim 14, wherein the anthraquinone dye is1,5-bis((2,2-dimethyl-3-hydroxypropyl)amino)-4,8-bis((4-methylphenyl)thio)anthraquinone.
 22. A radiation-curable composition, comprising: (a) anon-chromophore-containing, radiation-curable oligomer; and (b) aradiation-curable, chromophore-containing compound according to claim 6.23. The radiation-curable composition of claim 22, wherein thecomposition further comprises TiO₂.
 24. The radiation-curablecomposition of claim 22, wherein the composition further comprises oneor more of a photoinitiator, a reactive diluent, a stabilizer, and asurfactant.
 25. A substrate having the radiation-curable composition ofclaim 22 on at least a portion thereof.
 26. The substrate of claim 25,wherein the substrate is selected from the group consisting of (i) anoptical fiber having a core and a cladding surrounding the core, (ii) anoptical fiber having a core, a cladding surrounding the core, and one ormore polymeric coatings on the cladding, (iii) a plurality of opticalfibers arranged in an array, and (iv) an optical fiber ribbon.
 27. Amethod for producing a color-identifying, radiation-cured composition onat least a portion of a substrate, wherein the color-identifying,radiation-cured composition has at least one chromophore moietycovalently bonded to at least one other component of thecolor-identifying, radiation-cured composition, the method comprisingthe steps of: providing a substrate; providing a radiation-curablecomposition according to claim 22; applying the radiation-curablecomposition of claim 22 to at least a portion of the substrate; andsubjecting the applied composition for a suitable period of time toradiation of a suitable wavelength and intensity to cause curing of thecomposition into the color-identifying, radiation-cured composition. 28.The method of claim 27, wherein the substrate is selected from the groupconsisting of (i) an optical fiber having a core and a claddingsurrounding the core, (ii) an optical fiber having a core, a claddingsurrounding the core, and one or more polymeric coatings on thecladding, (iii) a plurality of optical fibers arranged in an array, and(iv) an optical fiber ribbon.
 29. A dye concentrate comprising theradiation-curable, chromophore-containing compound of claim 6 andtetrahydrofurfuryl acrylate (THFA).
 30. A radiation-curable composition,comprising: (a) a non-chromophore-containing, radiation-curableoligomer; and (b) a dye concentrate according to claim
 29. 31. Theradiation-curable composition of claim 30, wherein the compositionfurther comprises TiO₂.
 32. The radiation-curable composition of claim30, wherein the composition further comprises one or more of aphotoinitiator, a reactive diluent, a stabilizer, and a surfactant. 33.A substrate having the radiation-curable composition of claim 30 on atleast a portion thereof.
 34. The substrate of claim 33, wherein thesubstrate is selected from the group consisting of (i) an optical fiberhaving a core and a cladding surrounding the core, (ii) an optical fiberhaving a core, a cladding surrounding the core, and one or morepolymeric coatings on the cladding, (iii) a plurality of optical fibersarranged in an array, and (iv) an optical fiber ribbon.
 35. A method forproducing a color-identifying, radiation-cured composition on at least aportion of a substrate, wherein the color-identifying, radiation-curedcomposition has at least one chromophore moiety covalently bonded to atleast one other component of the color-identifying, radiation-curedcomposition, the method comprising the steps of: providing a substrate;providing a radiation-curable composition according to claim 30;applying the radiation-curable composition of claim 30 to at least aportion of the substrate; and subjecting the applied composition for asuitable period of time to radiation of a suitable wavelength andintensity to cause curing of the composition into the color-identifying,radiation-cured composition.
 36. The method of claim 35, wherein thesubstrate is selected from the group consisting of (i) an optical fiberhaving a core and a cladding surrounding the core, (ii) an optical fiberhaving a core, a cladding surrounding the core, and one or morepolymeric coatings on the cladding, (iii) a plurality of optical fibersarranged in an array, and (iv) an optical fiber ribbon.
 37. The dyeconcentrate of claim 29, wherein the dye concentrate comprises greaterthan 5 wt % chromophore moiety, based on the total weight of the dyeconcentrate.
 38. A radiation-curable composition, comprising: (a) anon-chromophore-containing, radiation-curable oligomer; and (b) a dyeconcentrate according to claim
 37. 39. The dye concentrate of claim 29,wherein the dye concentrate comprises from about 10 wt % to about 35 wt% of chromophore moiety, based on the total weight of the dyeconcentrate.
 40. A radiation-curable composition, comprising: (a) anon-chromophore-containing, radiation-curable oligomer; and (b) a dyeconcentrate according to claim
 39. 41. A dye concentrate comprising ablend of two or more radiation-curable, chromophore-containing compoundsaccording to claim 6 and tetrahydrofurfuryl acrylate (THFA), wherein atleast the chromophore moiety of a first radiation-curable,chromophore-containing compound according to claim 6 is different fromthe chromophore moiety of a second radiation-curable,chromophore-containing compound according to claim
 6. 42. Aradiation-curable composition, comprising: (a) anon-chromophore-containing, radiation-curable oligomer; and (b) a dyeconcentrate according to claim
 41. 43. A radiation-curable,chromophore-containing compound comprising at least oneradiation-curable group and at least one chromophore moiety, wherein theradiation-curable, chromophore-containing compound comprises thereaction product of: (a) a chromophore-containing compound comprising(i) at least one isocyanate-reactive functional group and (ii) the atleast one chromophore moiety; and (b) a radiation-curable compoundcomprising (i) at least one isocyanate group and (ii) the, at least oneradiation-curable group, wherein the at least one radiation-curablegroup of said radiation-curable, chromophore-containing compound iscovalently bonded to said radiation-curable, chromophore-containingcompound by at least one covalent bond formed by reacting an isocyanategroup (i) of said radiation-curable compound (b) with anisocyanate-reactive functional group (i) of said chromophore-containingcompound (a).
 44. The radiation-curable, chromophore-containing compoundof claim 43, wherein the at least one isocyanate-reactive functionalgroup (i) of said chromophore-containing compound (a) is selected fromthe group consisting of —OH, —NH₂ and —SH.
 45. The radiation-curable,chromophore-containing compound of claim 43, wherein the at least oneradiation-curable group (ii) of said radiation-curable compound (b)comprises ethylenic unsaturation.
 46. The radiation-curable,chromophore-containing compound of claim 45, wherein theethylenically-unsaturated, radiation-curable group (ii) of saidradiation-curable compound (b) comprises a meth(acrylate).
 47. Theradiation-curable, chromophore-containing compound of claim 43, whereinthe at least one radiation-curable group (ii) of said radiation-curablecompound (b) comprises an epoxy group.
 48. The radiation-curable,chromophore-containing compound of claim 43, wherein the at least onechromophore moiety (ii) of said chromophore-containing compound (a) is amethine dye.
 49. The radiation-curable, chromophore-containing compoundof claim 43, wherein the at least one chromophore moiety (ii) of saidchromophore-containing compound (a) is an azo dye.
 50. Theradiation-curable, chromophore-containing compound of claim 43, whereinthe at least one chromophore moiety (ii) of said chromophore-containingcompound (a) is an anthraquinone dye.
 51. The radiation-curable,chromophore-containing compound of claim 43, wherein thechromophore-containing compound (a) is an anthraquinone dye having theformula:

wherein R groups R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸ are eachindependently selected from the group consisting of hydrogen, amino,hydroxy, halogen, nitro, carboxylated alkali metal, sulfated alkalimetal and a hydrocarbyl group optionally containing one or moreheteroatoms, provided that at least two of R groups R¹ through R⁸ haveat least one isocyanate-reactive functional group selected from thegroup consisting of —OH, —NH₂ and —SH, and further wherein adjacent Rgroups from among R¹ through R⁸ can form a ring.
 52. Theradiation-curable, chromophore-containing compound of claim 51, whereinfrom 1 to 3 of said R groups R¹ through R⁸ have the following formula:

wherein R⁹ is hydrogen or an alkyl group having from 1 to about 12carbon atoms, X is —CH₂—, a is an integer from 1 to about 6, Yrepresents polymeric units of hydroxy alkylenes or alkylene oxidemonomers selected from the group consisting of ethylene oxide, propyleneoxide, butylene oxide, cyclohexane oxide, and glycidol, b is either 0 or1, and Z is —OH, —NH₂, or —SH group, and further wherein the remainderof said R groups R¹ through R⁸ are selected from the group consisting ofhydrogen, amino, hydroxy, halogen, nitro, carboxylated alkali metal andsulfated alkali metal.
 53. The radiation-curable, chromophore-containingcompound of claim 51, wherein the anthraquinone dye has the formula:

wherein R⁹ and R¹⁰ are independently selected from hydrogen or an alkylgroup having from 1 to about 12 carbon atoms, X is —CH₂—, a and a′independently are integers from 1 to about 6, Y and Y′ are independentlyrepresent polymeric units of hydroxy alkylenes or alkylene oxidemonomers selected from the group consisting of ethylene oxide, propyleneoxide, butylene oxide, cyclohexane oxide, and glycidol, b and b′ areindependently either 0 or 1, and Z and Z′ independently are —OH, —NH₂,or —SH groups.
 54. The radiation-curable, chromophore-containingcompound of claim 53, wherein the anthraquinone dye has the formula:

wherein n, n′, m, m′, p, and p′ independently have a value of from 0 toabout
 40. 55. The radiation-curable, chromophore-containing compound ofclaim 53, wherein the anthraquinone dye has the formula:


56. The radiation-curable, chromophore-containing compound of claim 43,wherein the chromophore-containing compound (a) is selected from thegroup consisting of1,5-bis((3-hydroxy-2,2-dimethylpropyl)amino)-9,10-anthracenedione;2,2′-((9,10-dihydro-9,10-dioxo-1,5-anthracenediyl)bis(thio))bis-benzoicacid, 2-hydroxyethyl ester; and1,5-bis((2,2-dimethyl-3-hydroxypropyl)amino)-4,8-bis((4-methylphenyl)thio)anthraquinone.
 57. The radiation-curable, chromophore-containingcompound of claim 56, wherein the chromophore-containing compound (a) is1,5-bis((2,2-dimethyl-3-hydroxypropyl)amino)-4,8-bis((4-methylphenyl)thio)anthraquinone.
 58. A radiation-curable composition, comprising: (a) anon-chromophore-containing, radiation-curable oligomer; and (b) aradiation-curable, chromophore-containing compound according to claim43.
 59. The radiation-curable composition of claim 58, wherein thecomposition further comprises TiO₂.
 60. The radiation-curablecomposition of claim 58, wherein the composition further comprises oneor more of a photoinitiator, a reactive diluent, a stabilizer, and asurfactant.
 61. A substrate having the radiation-curable composition ofclaim 58 on at least a portion thereof.
 62. The substrate of claim 61,wherein the substrate is selected from the group consisting of (i) anoptical fiber having a core and a cladding surrounding the core, (ii) anoptical fiber having a core, a cladding surrounding the core, and one ormore polymeric coatings on the cladding, (iii) a plurality of opticalfibers arranged in an array, and (iv) an optical fiber ribbon.
 63. Amethod for producing a color-identifying, radiation-cured composition onat least a portion of a substrate, wherein the color-identifying,radiation-cured composition has at least one chromophore moietycovalently bonded to at least one other component of thecolor-identifying, radiation-cured composition, the method comprisingthe steps of: providing a substrate; providing a radiation-curablecomposition according to claim 58; applying the radiation-curablecomposition of claim 58 to at least a portion of the substrate; andsubjecting the applied composition for a suitable period of time toradiation of a suitable wavelength and intensity to cause curing of thecomposition into the color-identifying, radiation-cured composition. 64.The method of claim 63, wherein the substrate is selected from the groupconsisting of (i) an optical fiber having a core and a claddingsurrounding the core, (ii) an optical fiber having a core, a claddingsurrounding the core, and one or more polymeric coatings on thecladding, (iii) a plurality of optical fibers arranged in an array, and(iv) an optical fiber ribbon.
 65. A dye concentrate comprising theradiation-curable, chromophore-containing compound of claim 43 andtetrahydrofurfuryl acrylate (THFA).
 66. A radiation-curable composition,comprising: (a) a non-chromophore-containing, radiation-curableoligomer; and (b) a dye concentrate according to claim
 65. 67. Theradiation-curable composition of claim 66, wherein the compositionfurther comprises TiO₂.
 68. The radiation-curable composition of claim66, wherein the composition further comprises one or more of aphotoinitiator, a reactive diluent, a stabilizer, and a surfactant. 69.A substrate having the radiation-curable composition of claim 66 on atleast a portion thereof.
 70. The substrate of claim 69, wherein thesubstrate is selected from the group consisting of (i) an optical fiberhaving a core and a cladding surrounding the core, (ii) an optical fiberhaving a core, a cladding surrounding the core, and one or morepolymeric coatings on the cladding, (iii) a plurality of optical fibersarranged in an array, and (iv) an optical fiber ribbon.
 71. A method forproducing a color-identifying, radiation-cured composition on at least aportion of a substrate, wherein the color-identifying, radiation-curedcomposition has at least one chromophore moiety covalently bonded to atleast one other component of the color-identifying, radiation-curedcomposition, the method comprising the steps of: providing a substrate;providing a radiation-curable composition according to claim 66;applying the radiation-curable composition of claim 66 to at least aportion of the substrate; and subjecting the applied composition for asuitable period of time to radiation of a suitable wavelength andintensity to cause curing of the composition into the color-identifying,radiation-cured composition.
 72. The method of claim 71, wherein thesubstrate is selected from the group consisting of (i) an optical fiberhaving a core and a cladding surrounding the core, (ii) an optical fiberhaving a core, a cladding surrounding the core, and one or morepolymeric coatings on the cladding, (iii) a plurality of optical fibersarranged in an array, and (iv) an optical fiber ribbon.
 73. The dyeconcentrate of claim 65, wherein the dye concentrate comprises greaterthan 5 wt % chromophore moiety, based on the total weight of the dyeconcentrate.
 74. A radiation-curable composition, comprising: (a) anon-chromophore-containing, radiation-curable oligomer; and (b) a dyeconcentrate according to claim
 73. 75. The dye concentrate of claim 65,wherein the dye concentrate comprises from about 10 wt % to about 35 wt% of chromophore moiety, based on the total weight of the dyeconcentrate.
 76. A radiation-curable composition, comprising: (a) anon-chromophore-containing, radiation-curable oligomer; and (b) a dyeconcentrate according to claim
 75. 77. A dye concentrate comprising ablend of two or more radiation-curable, chromophore-containing compoundsaccording to claim 43 and tetrahydrofurfuryl acrylate (THFA), wherein atleast the chromophore moiety of a first radiation-curable,chromophore-containing compound according to claim 43 is different fromthe chromophore moiety of a second radiation-curable,chromophore-containing compound according to claim
 43. 78. Aradiation-curable composition, comprising: (a) anon-chromophore-containing, radiation-curable oligomer; and (b) a dyeconcentrate according to claim
 77. 79. A radiation-curable,chromophore-containing compound comprising at least oneradiation-curable group and at least one chromophore moiety.
 80. Theradiation-curable, chromophore-containing compound of claim 79, whereinthe at least one radiation-curable group comprises ethylenicunsaturation.
 81. The radiation-curable, chromophore-containing compoundof claim 80, wherein the ethylenically-unsaturated, radiation-curablegroup comprises a meth(acrylate).
 82. The radiation-curable,chromophore-containing compound of claim 79, wherein the at least oneradiation-curable group comprises an epoxy group.
 83. Theradiation-curable, chromophore-containing compound of claim 79, whereinthe at least one chromophore moiety is a methine dye, and the methinedye comprises a methine core group with at least one substituentcomprising the at least one radiation-curable group.
 84. Theradiation-curable, chromophore-containing compound of claim 79, whereinthe at least one chromophore moiety is an azo dye, and the azo dyecomprises an azo core group with at least one substituent comprising theat least one radiation-curable group.
 85. The radiation-curable,chromophore-containing compound of claim 79, wherein the at least onechromophore moiety is an anthraquinone dye, and the anthraquinone dyecomprises an anthraquinone core group with at least one substituentcomprising the at least one radiation-curable group.
 86. Theradiation-curable, chromophore-containing compound of claim 85, whereinthe anthraquinone dye has the formula:

wherein R groups R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸ are eachindependently selected from the group consisting of hydrogen, amino,hydroxy, halogen, nitro, carboxylated alkali metal, sulfated alkalimetal and a hydrocarbyl group optionally containing one or moreheteroatoms, provided that at least one of R groups R¹¹ through R¹⁸comprises at least one ethylenically unsaturated radiation-curablegroup.
 87. The radiation-curable, chromophore-containing compound ofclaim 86, wherein one or two of said R groups R¹¹ through R¹⁸ have a(meth)acrylic functionality and at least four of said R groups R¹¹through R¹⁸ are hydrogen.
 88. The radiation-curable,chromophore-containing compound of claim 85, wherein the anthraquinonedye has one of the following formulas:

wherein R²⁹, R³⁰, R³¹, R³², R³³, and R³⁴ are the same or different andare independently hydrogen or a C₁ to C₆ alkyl optionally substitutedwith one or more substituents selected from the group consisting of —OH,—NH₂, —SH, —NO₂, —CN and halogen.
 89. A radiation-curable composition,comprising: (a) a non-chromophore-containing, radiation-curableoligomer; and (b) a radiation-curable, chromophore-containing compoundaccording to claim
 79. 90. The radiation-curable composition of claim89, wherein the composition further comprises TiO₂.
 91. Theradiation-curable composition of claim 89, wherein the compositionfurther comprises one or more of a photoinitiator, a reactive diluent, astabilizer, and a surfactant.
 92. A substrate having theradiation-curable composition of claim 89 on at least a portion thereof.93. The substrate of claim 92, wherein the substrate is selected fromthe group consisting of (i) an optical fiber having a core and acladding surrounding the core, (ii) an optical fiber having a core, acladding surrounding the core, and one or more polymeric coatings on thecladding, (iii) a plurality of optical fibers arranged in an array, and(iv) an optical fiber ribbon.
 94. A method for producing acolor-identifying, radiation-cured composition on at least a portion ofa substrate, wherein the color-identifying, radiation-cured compositionhas at least one chromophore moiety covalently bonded to at least oneother component of the color-identifying, radiation-cured composition,the method comprising the steps of: providing a substrate; providing aradiation-curable composition according to claim 89; applying theradiation-curable composition of claim 89 to at least a portion of thesubstrate; and subjecting the applied composition for a suitable periodof time to radiation of a suitable wavelength and intensity to causecuring of the composition into the color-identifying, radiation-curedcomposition.
 95. The method of claim 94, wherein the substrate isselected from the group consisting of (i) an optical fiber having a coreand a cladding surrounding the core, (ii) an optical fiber having acore, a cladding surrounding the core, and one or more polymericcoatings on the cladding, (iii) a plurality of optical fibers arrangedin an array, and (iv) an optical fiber ribbon.
 96. A dye concentratecomprising the radiation-curable, chromophore-containing compound ofclaim 79 and tetrahydrofurfuryl acrylate (THFA).
 97. A radiation-curablecomposition, comprising: (a) a non-chromophore-containing,radiation-curable oligomer; and (b) a dye concentrate according to claim96.
 98. The radiation-curable composition of claim 97, wherein thecomposition further comprises TiO₂.
 99. The radiation-curablecomposition of claim 97, wherein the composition further comprises oneor more of a photoinitiator, a reactive diluent, a stabilizer, and asurfactant.
 100. A substrate having the radiation-curable composition ofclaim 97 on at least a portion thereof.
 101. The substrate of claim 100,wherein the substrate is selected from the group consisting of (i) anoptical fiber having a core and a cladding surrounding the core, (ii) anoptical fiber having a core, a cladding surrounding the core, and one ormore polymeric coatings on the cladding, (iii) a plurality of opticalfibers arranged in an array, and (iv) an optical fiber ribbon.
 102. Amethod for producing a color-identifying, radiation-cured composition onat least a portion of a substrate, wherein the color-identifying,radiation-cured composition has at least one chromophore moietycovalently bonded to at least one other component of thecolor-identifying, radiation-cured composition, the method comprisingthe steps of: providing a substrate; providing a radiation-curablecomposition according to claim 97; applying the radiation-curablecomposition of claim 97 to at least a portion of the substrate; andsubjecting the applied composition for a suitable period of time toradiation of a suitable wavelength and intensity to cause curing of thecomposition into the color-identifying, radiation-cured composition.103. The method of claim 102, wherein the substrate is selected from thegroup consisting of (i) an optical fiber having a core and a claddingsurrounding the core, (ii) an optical fiber having a core, a claddingsurrounding the core, and one or more polymeric coatings on thecladding, (iii) a plurality of optical fibers arranged in an array, and(iv) an optical fiber ribbon.
 104. The dye concentrate of claim 96,wherein the dye concentrate comprises greater than 5 wt % chromophoremoiety, based on the total weight of the dye concentrate.
 105. Aradiation-curable composition, comprising: (a) anon-chromophore-containing, radiation-curable oligomer; and (b) a dyeconcentrate according to claim
 104. 106. The dye concentrate of claim96, wherein the dye concentrate comprises from about 10 wt % to about 35wt % of chromophore moiety, based on the total weight of the dyeconcentrate.
 107. A radiation-curable composition, comprising: (a) anon-chromophore-containing, radiation-curable oligomer; and (b) a dyeconcentrate according to claim
 106. 108. A dye concentrate comprising ablend of two or more radiation-curable, chromophore-containing compoundsaccording to claim 79 and tetrahydrofurfuryl acrylate (THFA), wherein atleast the chromophore moiety of a first radiation-curable,chromophore-containing compound according to claim 79 is different fromthe chromophore moiety of a second radiation-curable,chromophore-containing compound according to claim
 79. 109. Aradiation-curable composition, comprising: (a) anon-chromophore-containing, radiation-curable oligomer; and (b) a dyeconcentrate according to claim
 108. 110. A radiation-curablecomposition, comprising: (a) a non-chromophore-containing,radiation-curable oligomer; and two or more of (b) a radiation-curable,chromophore-containing compound according to claim 6; (c) aradiation-curable, chromophore-containing compound according to claim43; and (d) a radiation-curable, chromophore-containing compoundaccording to claim
 79. 111. A dye concentrate comprisingtetrahydrofurfuryl acrylate (THFA) and two or more of aradiation-curable, chromophore-containing compound according to claim 6,a radiation-curable, chromophore-containing compound according to claim43, and a radiation-curable, chromophore-containing compound accordingto claim
 79. 112. A radiation-curable composition, comprising: (a) anon-chromophore-containing, radiation-curable oligomer; and (b) a dyeconcentrate according to claim
 111. 113. A colored oligomer forproviding color to a coating on a communications element, said coloredoligomer comprising the reaction product of: (a) an isocyanate endcapped oligomer, and (b) a radiation curable monomer having both (i) areactive functionality which is reactive with isocyanate and (ii)ethylenic unsaturation, wherein said colored oligomer is end capped withradiation curable groups by covalent linkages formed by reacting saidreactive functionality (i) of said radiation curable monomer (b) with anisocyanate moiety of said isocyanate end capped oligomer (a), and saidisocyanate end capped oligomer (a) is the reaction product of: (c) atleast one polyfunctional compound having at least two isocyanatereactive groups; and (d) at least one polyisocyanate, saidpolyfunctional compound (c) comprising at least one dye having at leasttwo isocyanate reactive functionalities.
 114. The colored oligomer ofclaim 113, wherein said dye is an anthraquinone dye and saidanthraquinone dye has the following formula:

wherein R groups R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸ are eachindependently selected from the group consisting of hydrogen, amino,hydroxy, halogen, nitro, carboxylated alkali metal, sulfated alkalimetal and a hydrocarbyl group optionally containing one or moreheteroatoms, provided that at least two of R groups R¹ through R⁸ haveat least one isocyanate reactive functionality selected from the groupconsisting of —OH, —NH₂ and —SH, and further wherein adjacent R groupsfrom among R¹ through R⁸ can form a ring.
 115. The colored oligomer ofclaim 114, wherein from 1 to 3 of said R groups R¹ through R⁸ have thefollowing formula:

wherein R⁹ is hydrogen or an alkyl group having from 1 to about 12carbon atoms, X is —CH₂—, a is an integer from 1 to about 6, Yrepresents polymeric units of hydroxy alkylenes or alkylene oxidemonomers selected from the group consisting of ethylene oxide, propyleneoxide, butylene oxide, cyclohexane oxide, and glycidol, b is either 0 or1, and Z is a reactive —OH, —NH₂, or —SH group, and further wherein theremainder of said R groups R¹ through R⁸ are selected from the groupconsisting of hydrogen, amino, hydroxy, halogen, nitro, carboxylatedalkali metal and sulfated alkali metal.
 116. The colored oligomer ofclaim 114, wherein said anthraquinone dye has the following formula:

wherein R⁹ and R¹⁰ are independently selected from hydrogen or an alkylgroup having from 1 to about 12 carbon atoms, X is —CH₂—, a and a′independently are integers from 1 to about 6, Y and Y′ are independentlyrepresent polymeric units of hydroxy alkylenes or alkylene oxidemonomers selected from the group consisting of ethylene oxide, propyleneoxide, butylene oxide, cyclohexane oxide, and glycidol, b and b′ areindependently either 0 or 1, and Z and Z′ independently are reactive—OH, —NH₂, or —SH groups.
 117. The colored oligomer of claim 116,wherein said isocyanate end capped oligomer (a) is a urethane oligomerand said anthraquinone dye has the following formula:

wherein n, n′, m, m′, p, and p′ independently have a value of from 0 toabout
 40. 118. The colored oligomer of claim 116, wherein saidanthraquinone dye has the formula


119. The colored oligomer of claim 114, wherein said anthraquinone dyeis selected from the group consisting of1,5-bis((3-hydroxy-2,2-dimethylpropyl)amino)-9,10-anthracenedione;2,2′-((9,10-dihydro-9,10-dioxo-1,5-anthracenediyl)bis(thio))bis-benzoicacid, 2-hydroxyethyl ester; and1,5-bis((2,2-dimethyl-3-hydroxypropyl)amino)-4,8-bis((4-methylphenyl)thio)anthraquinone.
 120. The colored oligomer of claim 114, wherein saidanthraquinone dye is1,5-bis((2,2-dimethyl-3-hydroxypropyl)amino)-4,8-bis((4-methylphenyl)thio)anthraquinone.
 121. The colored oligomer of claim 113 wherein a(meth)acrylic group represents the ethylenic unsaturation (ii) in theradiation curable monomer (b).
 122. A photocurable resin composition forforming a colored, cured coating on an optical fiber, said resincomposition comprising: (e) at least one (meth)acrylate end cappedurethane oligomer; (f) at least one photoinitiator; (g) at least onereactive diluent; and (h) at least one colored oligomer according toclaim
 113. 123. An optical fiber comprising a colored, cured coating,said colored, cured coating having been formed from the photocurableresin composition of claim
 122. 124. A reactive anthraquinone dye forproviding color to a coating on an optical fiber, said reactiveanthraquinone dye comprising an anthraquinone core group with at leastone substituent comprising a radiation curable group.
 125. The reactiveanthraquinone dye of claim 124, wherein said radiation curable group isan ethylenically unsaturated group or an epoxy group.
 126. The reactiveanthraquinone dye of claim 124, wherein said radiation curable group isa (meth)acrylic group.
 127. The reactive anthraquinone dye of claim 124,wherein said reactive anthraquinone dye has the following formula:

wherein R groups R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and R⁸ are eachindependently selected from the group consisting of hydrogen, amino,hydroxy, halogen, nitro, carboxylated alkali metal, sulfated alkalimetal and a hydrocarbyl group optionally containing one or moreheteroatoms, provided that at least one of R groups R¹¹ through R¹⁸ haveat least one ethylenically unsaturated radiation curable functionality.128. The reactive anthraquinone dye of claim 127, wherein one or two ofsaid R groups R¹¹ through R¹⁸ have a (meth)acrylic functionality and atleast four of said R groups R¹¹ through R¹⁸ are hydrogen.
 129. Thereactive anthraquinone dye of claim 127, wherein the reactiveanthraquinone dye has one of the following formulas:

wherein R²⁹, R³⁰, R³¹, R³², R³³, and R³⁴ are the same or different andare independently hydrogen or a C₁ to C₆ alkyl optionally substitutedwith one or more substituents selected from the group consisting of —OH,—NH₂, —SH, —NO₂, —CN and halogen.
 130. A photocurable resin compositionfor forming a colored, cured coating on an optical fiber, said resincomposition comprising: (a) at least one (meth)acrylate end cappedurethane oligomer; (b) at least one photoinitiator; (c) at least onereactive diluent; and (d) at least one reactive anthraquinone dyeaccording to claim
 127. 131. An optical fiber comprising a colored,cured coating, said colored, cured coating having been formed from thephotocurable resin composition of claim 130.